Herbicides

ABSTRACT

Compounds of formula (I) wherein the substituents are as defined in claim  1 , are suitable for use as herbicides.

This application is a 371 of International Application No.PCT/EP2008/006467 filed Aug. 6, 2008, which claims priority to GB0715454.5 filed Aug. 8, 2007, the contents of which are incorporatedherein by reference.

The present invention relates to novel, herbicidally activecyclopentanedione compounds, and derivatives thereof, to processes fortheir preparation, to compositions comprising those compounds, and totheir use in controlling weeds, especially in crops of useful plants, orin inhibiting undesired plant growth.

Cyclopentanedione compounds having herbicidal action are described, forexample, in WO 01/74770 and WO 96/03366.

Novel cyclopentanedione compounds, and derivatives thereof, havingherbicidal and growth-inhibiting properties have now been found.

The present invention accordingly relates to compounds of formula I

whereinG is hydrogen or an alkali metal, alkaline earth metal, sulfonium,ammonium or a latentiating group,R¹ is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, halomethyl,haloethyl, vinyl, ethynyl, halogen, C₁-C₂alkoxy or C₁-C₂haloalkoxy,R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl,n-propyl, isopropyl, cyclopropyl, halomethyl, haloethyl, vinyl, ethynyl,halogen, C₁-C₂alkoxy or C₁-C₂ haloalkoxy,R⁵ and R¹² are independently of each other hydrogen, C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkyoxy, C₁-C₃alkylthio, halogen orC₁-C₆alkoxycarbonyl, orR⁵ and R¹² join together to form a 3-7 membered carbocyclic ring,optionally containing an oxygen or sulfur atom, andR⁶, R⁷, R⁸, R⁹, R¹⁰ and R¹¹ are independently of each other hydrogen ora substituent, or R⁷ and R⁸, or R⁹ and R¹⁰, together with the carbonatoms to which they are attached form a keto, an optionally substitutedalkenyl or optionally substituted imino unit, or any two of R⁷, R⁸, R⁹and R¹⁰ together form a 3-8 membered carbocyclic ring optionallycontaining a heteroatom selected from O, S or N and optionallysubstituted, or R⁷ and R¹⁰ together form a bond.

In the substituent definitions of the compounds of the formula I, eachalkyl moiety either alone or as part of a larger group (such as alkoxy,alkylthio, alkoxycarbonyl, alkylcarbonyl, alkylaminocarbonyl,dialkylaminocarbonyl) is a straight or branched chain and is, forexample, methyl, ethyl, n-propyl, n-butyl, n-pentyl, n-hexyl, isopropyl,n-butyl, sec-butyl, isobutyl, tert-butyl or neopentyl. The alkyl groupsare suitably C₁-C₆ alkyl groups, but are preferably C₁-C₄ alkyl or C₁-C₃alkyl groups, and, more preferably, C₁-C₂alkyl groups.

When present, the optional substituents on an alkyl moiety (alone or aspart of a larger group such as alkoxy, alkoxycarbonyl, alkylcarbonyl,alkylaminocarbonyl, dialkylaminocarbonyl) include one or more ofhalogen, nitro, cyano, C₃₋₇ cycloalkyl (itself optionally substitutedwith C₁₋₆ alkyl or halogen), C₅₋₇ cycloalkenyl (itself optionallysubstituted with C₁₋₆ alkyl or halogen), hydroxy, C₁₋₁₀ alkoxy, C₁₋₁₀alkoxy(C₁₋₁₀)alkoxy, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy, C₁₋₆alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)-alkoxy (wherethe aryl group is optionally substituted), C₃₋₇ cycloalkyloxy (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),C₃₋₁₀ alkenyloxy, C₃₋₁₀ alkynyloxy, mercapto, C₁₋₁₀ alkylthio, C₁₋₁₀haloalkylthio, aryl(C₁₋₄)alkylthio (where the aryl group is optionallysubstituted), C₃₋₇ cycloalkylthio (where the cycloalkyl group isoptionally substituted with C₁₋₆ alkyl or halogen),tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, arylthio (where the aryl group isoptionally substituted), C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl,C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl (where the arylgroup may be optionally substituted), tri(C₁₋₄) alkylsilyl,aryldi(C₁₋₄)alkylsilyl, triarylsilyl, aryl(C₁₋₄)alkylthio(C₁₋₄)alkyl,aryloxy(C₁₋₄)alkyl, formyl, C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆alkyl)aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₄ alkoxy)aminocarbonyl, C₁₋₆alkylcarbonyloxy, arylcarbonyloxy (where the aryl group is optionallysubstituted), di(C₁₋₆)alkylaminocarbonyloxy, C₁₋₆alkyliminooxy,C₃₋₆alkenyloxyimino, aryloxyimino, aryl (itself optionally substituted),heteroaryl (itself optionally substituted), heterocyclyl (itselfoptionally substituted with C₁₋₆ alkyl or halogen), aryloxy (where thearyl group is optionally substituted), heteroaryloxy, (where theheteroaryl group is optionally substituted), heterocyclyloxy (where theheterocyclyl group is optionally substituted with C₁₋₆ alkyl orhalogen), amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆alkylcarbonylamino, N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino, C₂₋₆alkenylcarbonyl, C₂₋₆ alkynylcarbonyl, C₃₋₆ alkenyloxycarbonyl, C₃₋₆alkynyloxycarbonyl, aryloxycarbonyl (where the aryl group is optionallysubstituted) and arylcarbonyl (where the aryl group is optionallysubstituted).

Alkenyl and alkynyl moieties can be in the form of straight or branchedchains, and the alkenyl moieties, where appropriate, can be of eitherthe (E)- or (Z)-configuration. Examples are vinyl, allyl and propargyl.Alkenyl and alkynyl moieties can contain one or more double and/ortriple bonds in any combination. It is understood, that allenyl andalkylinylalkenyl are included in these terms. It is to be understoodthat the alkenyl units formed by R⁷ together with R⁸ are directlyattached to the bridged cyclohexane ring by a double bond.

When present, the optional substituents on alkenyl or alkynyl includethose optional substituents given above for an alkyl moiety.

Halogen is fluorine, chlorine, bromine or iodine.

Haloalkyl groups are alkyl groups which are substituted with one or moreof the same or different halogen atoms and are, for example, CF₃, CF₂C₁,CF₂H, CCl₂H, FCH₂, ClCH₂, BrCH₂, CH₃CHF, (CH₃)₂CF, CF₃CH₂ or CHF₂CH₂.

In the context of the present specification the term “aryl” refers toring systems which may be mono-, bi- or tricyclic. Examples of suchrings include phenyl, naphthyl, anthracenyl, indenyl or phenanthrenyl. Apreferred aryl group is phenyl.

The term “heteroaryl” preferably refers to an aromatic ring systemcontaining at least one heteroatom and consisting either of a singlering or of two or more fused rings. Preferably, single rings willcontain up to three and bicyclic systems up to four heteroatoms whichwill preferably be chosen from nitrogen, oxygen and sulphur. Examples ofsuch groups include furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl,isothiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl,1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl,1,2,5-thiadiazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl,1,2,3-triazinyl, 1,2,4-triazinyl, 1,3,5-triazinyl, benzofuryl,benzisofuryl, benzothienyl, benzisothienyl, indolyl, isoindolyl,indazolyl, benzothiazolyl, benzisothiazolyl, benzoxazolyl,benzisoxazolyl, benzimidazolyl, 2,1,3-benzoxadiazole, quinolinyl,isoquinolinyl, cinnolinyl, phthalazinyl, quinazolinyl, quinoxalinyl,naphthyridinyl, benzotriazinyl, purinyl, pteridinyl and indolizinyl.

Preferred examples of heteroaromatic radicals include pyridyl,pyrimidinyl, triazinyl, thienyl, furyl, oxazolyl, isoxazolyl,2,1,3-benzoxadiazolyl and thiazolyl.

Another group of preferred heteroaryls comprises furyl, thienyl,pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl,pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, cinnolinyl,quinazolinyl or quinoxalinyl.

The term “heterocyclyl” preferably refers to a non-aromatic preferablymonocyclic or bicyclic ring systems containing up to 7 atoms includingone or more (preferably one or two) heteroatoms selected from O, S andN. Examples of such rings include 1,3-dioxolane, oxetane,tetrahydrofuran, morpholine, thiomorpholin and piperazine. When present,the optional substituents on heterocyclyl include C₁₋₆ alkyl and C₁₋₆haloalkyl as well as those optional substituents given above for analkyl moiety.

Cycloalkyl includes preferably cyclopropyl, cyclobutyl, cyclopentyl andcyclohexyl. Cycloalkylalkyl is preferentially cyclopropylmethyl.Cycloalkenyl includes preferably cyclopentenyl and cyclohexenyl. Whenpresent, the optional substituents on cycloalkyl or cycloalkenyl includeC₁₋₃ alkyl as well as those optional substituents given above for analkyl moiety.

Carbocyclic rings such as those formed by R⁷ together with R⁸ includearyl, cycloalkyl or carbocyclic groups, and cycloalkenyl groups.

When present, the optional substituents on aryl, heteroaryl andcarbocycles are preferably selected independently, from halogen, nitro,cyano, rhodano, isothiocyanato, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆alkoxy-(C₁₋₆)alkyl, C₂₋₆ alkenyl, C₂₋₄ haloalkenyl, C₂₋₄ alkynyl, C₃₋₇cycloalkyl (itself optionally substituted with C₁₋₆ alkyl or halogen),C₅₋₇ cycloalkenyl (itself optionally substituted with C₁₋₆ alkyl orhalogen), hydroxy, C₁₋₁₀ alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy,tri(C₁₋₄)alkylsilyl(C₁₋₄)alkoxy, C₁₋₆ alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀haloalkoxy, aryl(C₁₋₄)alkoxy (where the aryl group is optionallysubstituted with halogen or C₁₋₆ alkyl), C₃₋₇ cycloalkyloxy (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),C₃₋₁₀ alkenyloxy, C₃₋₁₀ alkynyloxy, mercapto, C₁₋₁₀ alkylthio, C₁₋₁₀haloalkylthio, aryl(C₁₋₄)alkylthio, C₃₋₇ cycloalkylthio (where thecycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen),tri(C₁₋₄)-alkylsilyl(C₁₋₆)alkylthio, arylthio, C₁₋₄ alkylsulfonyl, C₁₋₆haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl,arylsulfonyl, tri(C₁₋₄)alkylsilyl, aryldi(C₁₋₄)-alkysilyl,(C₁₋₄)alkyldiarylsilyl, triarylsilyl, C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆alkyl)-aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆alkylcarbonyloxy, arylcarbonyloxy, di(C₁₋₆)alkylamino-carbonyloxy, aryl(itself optionally substituted with C₁₋₆ alkyl or halogen), heteroaryl(itself optionally substituted with C₁₋₆ alkyl or halogen), heterocyclyl(itself optionally substituted with C₁₋₆ alkyl or halogen), aryloxy(where the aryl group is optionally substituted with C₁₋₆ alkyl orhalogen), heteroaryloxy (where the heteroaryl group is optionallysubstituted with C₁₋₆ alkyl or halogen), heterocyclyloxy (where theheterocyclyl group is optionally substituted with C₁₋₆ alkyl orhalogen), amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆alkylcarbonylamino, N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino,arylcarbonyl, (where the aryl group is itself optionally substitutedwith halogen or C₁₋₆ alkyl) or two adjacent positions on an aryl orheteroaryl system may be cyclised to form a 5, 6 or 7 memberedcarbocyclic or heterocyclic ring, itself optionally substituted withhalogen or C₁₋₆ alkyl. Further substituents for aryl or heteroarylinclude arylcarbonylamino (where the aryl group is substituted by C₁₋₆alkyl or halogen),(C₁₋₆)alkoxycarbonylamino(C₁₋₆)alkoxycarbonyl-N—(C₁₋₆)alkylamino,aryloxycarbonylamino (where the aryl group is substituted by C₁₋₆ alkylor halogen), aryloxycarbonyl-N—(C₁₋₆)alkylamino, (where the aryl groupis substituted by C₁₋₆ alkyl or halogen), arylsulphonylamino (where thearyl group is substituted by C₁₋₆ alkyl or halogen),arylsulphonyl-N—(C₁₋₆)alkylamino (where the aryl group is substituted byC₁₋₆ alkyl or halogen), aryl-N—(C₁₋₆)alkylamino (where the aryl group issubstituted by C₁₋₆ alkyl or halogen), arylamino (where the aryl groupis substituted by C₁₋₆ alkyl or halogen), heteroaryl amino (where theheteroaryl group is substituted by C₁₋₆ alkyl or halogen),heterocyclylamino (where the heterocyclyl group is substituted by C₁₋₆alkyl or halogen), aminocarbonylamino, C₁₋₆ alkylaminocarbonylamino,di(C₁₋₆)alkylaminocarbonylamino, arylaminocarbonylamino where the arylgroup is substituted by C₁₋₆ alkyl or halogen),aryl-N—(C₁₋₆)alkylamino-carbonylamino where the aryl group issubstituted by C₁₋₆ alkyl or halogen), C₁₋₆alkylaminocarbonyl-N—(C₁₋₆)alkylamino,di(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkylamino,arylaminocarbonyl-N—(C₁₋₆)alkylamino where the aryl group is substitutedby C₁₋₆ alkyl or halogen) andaryl-N—(C₁₋₆)alkylaminocarbonyl-N—(C₁₋₆)alkylamino where the aryl groupis substituted by C₁₋₆ alkyl or halogen).

For substituted heterocyclyl groups it is preferred that one or moresubstituents are independently selected from halogen, C₁₋₆ alkyl, C₁₋₆haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆alkylsulfinyl, C₁₋₆ alkylsulfonyl, nitro and cyano. It is to beunderstood that dialkylamino substituents include those where thedialkyl groups together with the N atom to which they are attached forma five, six or seven-membered heterocyclic ring which may contain one ortwo further heteroatoms selected from O, N or S and which is optionallysubstituted by one or two independently selected (C₁₋₆)alkyl groups.When heterocyclic rings are formed by joining two groups on an N atom,the resulting rings are suitably pyrrolidine, piperidine, thiomorpholineand morpholine each of which may be substituted by one or twoindependently selected (C₁₋₆) alkyl groups.

It should be understood that the term “substituent” in the definitionsof R⁶ to R¹¹ comprises preferably all substitutents given above for“aryl”, “heteroaryl” and “heterocyclyl”.

The invention relates also to the salts which the compounds of formula Iare able to form with amines, alkali metal and alkaline earth metalbases or quaternary ammonium bases. Among the alkali metal and alkalineearth metal hydroxides as salt formers, special mention should be madeof the hydroxides of lithium, sodium, potassium, magnesium and calcium,but especially the hydroxides of sodium and potassium. The compounds offormula I according to the invention also include hydrates which may beformed during the salt formation.

Examples of amines suitable for ammonium salt formation include ammoniaas well as primary, secondary and tertiary C₁-C₁₈alkylamines,C₁-C₄hydroxyalkylamines and C₂-C₄-alkoxyalkylamines, for examplemethylamine, ethylamine, n-propylamine, isopropylamine, the fourbutylamine isomers, n-amylamine, isoamylamine, hexylamine, heptylamine,octylamine, nonylamine, decylamine, pentadecylamine, hexadecylamine,heptadecylamine, octadecylamine, methylethylamine, methylisopropylamine,methylhexylamine, methylnonylamine, methylpentadecylamine,methyloctadecylamine, ethylbutylamine, ethylheptylamine,ethyloctylamine, hexylheptylamine, hexyloctylamine, dimethylamine,diethylamine, di-n-propylamine, diisopropylamine, di-n-butylamine,di-n-amylamine, diisoamylamine, dihexylamine, diheptylamine,dioctylamine, ethanolamine, n-propanolamine, isopropanolamine,N,N-diethanolamine, N-ethylpropanolamine, N-butylethanolamine,allylamine, n-but-2-enylamine, n-pent-2-enylamine,2,3-dimethylbut-2-enylamine, dibut-2-enylamine, n-hex-2-enylamine,propylenediamine, trimethylamine, triethylamine, tri-n-propylamine,triisopropylamine, tri-n-butylamine, triisobutylamine,tri-sec-butylamine, tri-n-amylamine, methoxyethylamine andethoxyethylamine; heterocyclic amines, for example pyridine, quinoline,isoquinoline, morpholine, piperidine, pyrrolidine, indoline,quinuclidine and azepine; primary arylamines, for example anilines,methoxyanilines, ethoxyanilines, o-, m- and p-toluidines,phenylenediamines, benzidines, naphthylamines and o-, m- andp-chloroanilines; but especially triethylamine, isopropylamine anddiisopropylamine.

Preferred quaternary ammonium bases suitable for salt formationcorrespond, for example, to the formula [N(R_(a)R_(b)R_(c)R_(d))]OHwherein R_(a), R_(b), R_(c) and R_(d) are each independently of theothers C₁-C₄alkyl. Further suitable tetraalkylammonium bases with otheranions can be obtained, for example, by anion exchange reactions.

The latentiating groups G are selected to allow its removal by one or acombination of biochemical, chemical or physical processes to affordcompounds of formula I where G is H before, during or followingapplication to the treated area or plants. Examples of these processesinclude enzymatic cleavage, chemical hydrolysis and photoloysis.Compounds bearing such groups G may offer certain advantages, such asimproved penetration of the cuticula of the plants treated, increasedtolerance of crops, improved compatibility or stability in formulatedmixtures containing other herbicides, herbicide safeners, plant growthregulators, fungicides or insecticides, or reduced leaching in soils.

Preferably, in the compounds of the formula I, R⁶ and R¹¹ areindependently of each other hydrogen, halogen, formyl, cyano or nitro or

R⁶ and R¹¹ are independently of each other C₁-C₆alkyl, C₂-C₆alkenyl,C₂-C₆alkynyl, C₁-C₆alkoxy, C₃-C₇ cycloalkyl, C₃-C₇ cycloalkenyl, phenyl,heteroaryl or a 3-7 membered heterocyclyl, where all these substituentsare optionally substituted, or

R⁶ and R¹¹ are independently of each other a group COR¹³, CO₂R¹⁴ orCONR¹⁵R¹⁶, CR¹⁷═NOR¹⁸, CR¹⁹═NNR²⁰R²¹, NHR²², NR²²R²³ or OR²⁴, wherein

R¹³ is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇ cycloalkyl,C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl,where all these substituents are optionally substituted,

R¹⁴ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or is 3-7 memberedheterocyclyl, where all these substituents are optionally substituted,

R¹⁵ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroarylor a 3-7 membered heterocyclyl, where all these substituents areoptionally substituted,

R¹⁶ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl,C₁-C₆alkylsulfonyl, phenylsulfonyl, heteroarylsulfonyl, amino,C₁-C₆alkylamino, diC₁-C₆alkylamino, phenyl, heteroaryl or a 3-7 memberedheterocyclyl, where all these substituents are optionally substituted,orR¹⁵ and R¹⁶ may be joined to form an optionally substituted 3-7 memberedring, optionally containing an oxygen, sulfur or nitrogen atom,R¹⁷ and R¹⁹ are independently of each other hydrogen, C₁-C₃alkyl orC₃-C₆cycloalkyl,R¹⁸, R²⁰ and R²¹ are independently of each other hydrogen, C₁-C₆alkyl,C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, aminocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, phenyl orheteroaryl, where all these substituents are optionally substituted,R²² is C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl,phenylcarbonyl, phenoxycarbonyl, phenylaminocarbonyl,phenylthiocarbonyl, phenylsulfonyl, heteroarylcarbonyl,heteroaryloxycarbonyl, heteroarylaminocarbonyl, heteroarylthiocarbonylor heteroarylsulfonyl, where all these substituents are optionallysubstituted,R²³ is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl,phenyl or heteroaryl, where all these substituents are optionallysubstituted, or R²² and R²³ may be joined to form an optionallysubstituted 3-7 membered ring, optionally containing an oxygen, sulfuror nitrogen atom, where all these substituents are optionallysubstituted, andR²⁴ is C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, aminocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl,tri(C₁-C₆alkyl)silyl, phenyl or heteroaryl, where all these substituentsare optionally substituted.

More preferably, R⁶ and R¹¹ are independently of each other hydrogen,halogen, cyano, optionally substituted C₁-C₆alkyl or a group COR¹³,CO₂R¹⁴ or CONR¹⁵R¹⁶, CR¹⁷═NOR¹⁸ or CR¹⁹═NNR²⁰R²¹, wherein

R¹³, R¹⁴, R¹⁵ and R¹⁶ are C₁-C₆alkyl,

R¹⁷ and R¹⁹ are hydrogen or C₁-C₃ alkyl,

R¹⁸ is C₁-C₃ alkyl, and

R²⁰ and R²¹ are independently of each other hydrogen or C₁-C₃alkyl.

In particular, R⁶ and R¹¹ are independently of each other hydrogen,methyl or methyl substituted by C₁-C₃alkoxy.

Preferably, R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen,halogen, hydroxyl, formyl, amino, cyano or nitro, or

R⁷, R⁸, R⁹ and R¹⁰ are independently of each other C₁-C₆alkyl,C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl,C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl,C₁-C₆alkylthioC₁-C₆alkyl, C₁-C₆alkylsulfinylC₁-C₆alkyl,C₁-C₆alkylsulfonylC₁-C₆alkyl, C₃-C₇ cycloalkyl, C₄-C₇cycloalkenyl,tri(C₁-C₆alkyl)silyl, aryl, heteroaryl or a 3-7 membered heterocyclyl,where all these substituents are optionally substituted, orR⁷, R⁸, R⁹ and R¹⁰ are independently of each other a group COR¹³, CO₂R¹⁴or CONR¹⁵R¹⁶, CR¹⁷═NOR¹⁸, CR¹⁹═NNR²⁰R²¹, NR²²R²³ or OR²⁴, whereinR¹³ is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇ cycloalkyl,C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl,where all these substituents are optionally substituted,R¹⁴ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or is 3-7 memberedheterocyclyl, where all these substituents are optionally substituted,R¹⁵ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroarylor a 3-7 membered heterocyclyl, where all these substituents areoptionally substituted,R¹⁶ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy,C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl,C₁-C₆alkylsulfonyl, amino, C₁-C₆alkylamino, diC₁-C₆alkylamino, phenyl,heteroaryl or a 3-7 membered heterocyclyl, where all these substituentsare optionally substituted, orR¹⁵ and R¹⁶ may be joined to form an optionally substituted 3-7 memberedring, optionally containing an oxygen, sulfur or nitrogen atom,R¹⁷ and R¹⁹ are independently of each other hydrogen, C₁-C₃alkyl orC₃-C₆cycloalkyl,R¹⁸, R²⁰ and R²¹ are independently of each other hydrogen, C₁-C₆alkyl,C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl,diC₁-C₆alkylaminocarbonyl, phenyl or heteroaryl, where all thesesubstituents are optionally substituted,R²² and R²³ are independently of each other C₁-C₆alkyl, C₃-C₆alkenyl,C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl,C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl,diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl, phenyl or heteroaryl orR²² and R²³ may be joined to form an optionally substituted 3-7 memberedring, optionally containing an oxygen, sulfur or nitrogen atom, whereall these substituents are optionally substituted, andR²⁴ is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl,C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl,tri(C₁-C₆alkyl)silyl, phenyl or heteroaryl, where all these substituentsare optionally substituted.

More preferably, R⁷, R⁸, R⁹ and R¹⁰ are hydrogen.

It is also preferred that one of R⁷, R⁸, R⁹ and R¹⁰ is methyl or ethyl.

It is also preferred that one of R⁷, R⁸, R⁹ and R¹⁰ is an optionallysubstituted aryl or heteroaryl and more preferably optionallysubstituted phenyl, naphthyl, furyl, thienyl, pyrazolyl,1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl, pyridazinyl,pyrazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl orquinoxalinyl.

In particular, one of R⁷, R⁸, R⁹ and R¹⁰ is pyridyl or pyridylsubstituted by trifluoromethyl or halogen.

It is also preferred that R⁷ and R¹⁰ form a bond.

Preferably, R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen,cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl,C₁-C₆alkylthioC₁-C₆alkyl, C₁-C₆alkylsulfinylC₁-C₆alkyl,C₁-C₆alkylsulfonylC₁-C₆alkyl, 3-7 membered heterocyclyl, optionallysubstituted phenyl or optionally substituted heteroaryl, or CR¹⁷═NOR¹⁸,wherein

R¹⁷ is hydrogen or C₁-C₃ alkyl and

R¹⁸ is C₁-C₃ alkyl.

In another group of preferred compounds of the formula I, R⁷ and R⁸, orR⁹ and R¹⁰, together form a unit ═O, or form a unit ═CR²⁵R²⁶, or form aunit ═NR²⁷, or any two of R⁷, R⁸, R⁹ and R¹⁰ form a 3-8 membered ring,optionally containing a heteroatom selected from O, S or N andoptionally substituted by C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkyl, halogen, phenyl,phenyl substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy,C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl,C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, aminocarbonyl,C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, halogen, cyano or bynitro, heteroaryl or heteroaryl substituted by C₁-C₄alkyl,C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio,C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylcarbonyl, halogen,cyano or by nitro, wherein

R²⁵ and R²⁶ are independently of each other hydrogen, halogen, cyano ornitro, or

R²⁵ and R²⁶ are independently of each other C₁-C₆alkyl, C₁-C₆alkoxy,C₁-C₆alkylamino, diC₁-C₆alkylamino, C₁-C₆alkylcarbonyl,C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl,N-phenyl-N—C₁-C₆alkylaminocarbonyl,N-phenylC₁-C₆alkyl-N—C₁-C₆alkylaminocarbonyl,N-heteroaryl-N—C₁-C₆alkylaminocarbonyl,N-heteroarylC₁-C₆alkyl-N—C₁-C₆alkylaminocarbonyl, phenyl, heteroaryl,C₃-C₆cycloalkyl or 3-7 membered heterocyclyl, where all thesesubstituents are optionally substituted, orR²⁵ and R²⁶ may be joined together to form a 5-8 membered ringoptionally containing a heteroatom selected from O, S or N andoptionally substituted by C₁-C₂alkyl or C₁-C₂alkoxy,R²⁷ is nitro or cyano, orR²⁷ is C₁-C₆alkylamino, diC₁-C₆alkylamino, C₁-C₆alkoxy, C₃-C₆alkenyloxy,C₃-C₆alkynyloxy, phenoxy, phenylamino, N-phenyl-N—C₁-C₆alkylamino,N-phenylC₁-C₆alkyl-N—C₁-C₆alkylamino heteroaryloxy, heteroarylamino,N-heteroaryl-N—C₁-C₆alkylamino orN-heteroarylC₁-C₆alkyl-N—C₁-C₆alkylamino, where all these substituentsare optionally substituted,where, more preferably, R⁷ and R⁸, or R⁹ and R¹⁰, together form a unit═O or ═NR²⁷,wherein R²⁷ is C₁₋₃alkoxy or C₂-C₃ alkenyloxy.

More preferably, R⁷, R⁸, R⁹ and R¹⁰ are independently of each otherhydrogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₁-C₆alkoxy,C₁-C₆alkoxyC₁-C₆alkyl, 3-7 membered heterocyclyl, optionally substitutedphenyl or optionally substituted heteroaryl.

In particular, R⁷, R⁸, R⁹ and R¹⁰ are independently of each otherhydrogen, methyl, ethyl or optionally substituted phenyl.

In particular, one of R⁷, R⁸, R⁹ and R¹⁰ is optionally substitutedheteroaryl, preferably optionally substituted furyl, thienyl, pyrazolyl,1,2,4-triazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl,quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl or quinoxalinyl,

and more preferably pyridyl substituted once or twice by trifluoromethylor halogen.

In another group of preferred compounds of the formula I, R¹, R² and R⁴are methyl and R³ is hydrogen.

In another group of preferred compounds of the formula I, R¹, R² and R⁴are methyl and R³ is hydrogen, and

R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen, cyano,C₁-C₆alkyl, C₂-C₆alkenyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl, 3-7membered heterocyclyl, optionally substituted aryl or optionallysubstituted heteroaryl, preferably optionally substituted heteroaryl,and in particular pyridyl substituted once or twice by trifluoromethylor halogen.

In another group of preferred compounds of the formula I, R⁵ and R¹² areindependently of each other hydrogen or C₁-C₃alkyl, where hydrogen ismore preferred.

In another group of preferred compounds of the formula I, R¹ is methyl,ethyl, vinyl, ethynyl, cyclopropyl, difluoromethoxy, trifluoromethoxy orC₁-C₂ alkoxy and

R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl,vinyl or ethynyl.

Preferably in this group, R¹ is ethyl and R², R³ and R⁴ areindependently of each other hydrogen, methyl or ethyl.

Preferably in this group, R¹, R² and R⁴ are methyl and R³ is hydrogen.

The latentiating group G is preferably selected from the groups C₁-C₈alkyl, C₂-C₈ haloalkyl, phenylC₁-C₈alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), heteroarylC₁-C₈alkyl(wherein the heteroaryl may optionally be substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro),C₃-C₈ alkenyl, C₃-C₈ haloalkenyl, C₃-C₈ alkynyl, C(X^(a))—R^(a),C(X^(b))—X^(c)—R^(b), C(X^(d))—N(R^(c))—R^(d), —SO₂—R^(e),—P(X^(e))(R^(f))—R^(g) or CH₂—X^(f)—R^(h) wherein X^(a), X^(b), X^(c),X^(d), X^(e) and X^(f) are independently of each other oxygen or sulfur;

R^(a) is H, C₁-C₁₈alkyl, C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₆alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynylC₁-C₅oxyalkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₆alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, R^(b) isC₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₃-C₁₈alkynyl, C₂-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₆alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₆alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₃-C₅haloalkenyl,C₃-C₆cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,R^(c) and R^(d) are each independently of each other hydrogen,C₁-C₁₀alkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₂-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₂-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl,C₁-C₆alkylcarbonylC₁-C₅alkyl, C₁-C₆alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₂-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₂-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl, (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₂-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₆haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₂-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, heteroarylaminoor heteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, diheteroarylaminoor diheteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro, phenylamino orphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or by nitro, diphenylamino ordiphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen, cyano or by nitro or C₃-C₇cycloalkylamino,di-C₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy or R^(c) and R^(d) may jointogether to form a 3-7 membered ring, optionally containing oneheteroatom selected from O or S,R^(e) is C₁-C₁₀alkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₆alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₆alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl,C₃-C₈trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro,heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or bynitro, diheteroarylamino or diheteroarylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano ornitro, phenylamino or phenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,diphenylamino, or diphenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy,C₁-C₁₀alkoxy, C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₅dialkylaminoR^(f) and R^(g) are are each independently of each other C₁-C₁₀alkyl,C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₁-C₁₀alkoxy, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl,C₁-C₆alkylaminoC₁-C₅alkyl, C₂-C₅dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₅alkylideneaminoxyC₁-C₅alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl,C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl,N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl,halogen, cyano, or by nitro), heteroarylC₁-C₅alkyl (wherein theheteroaryl may optionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl,C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro), C₂-C₅haloalkenyl,C₃-C₈cycloalkyl, phenyl or phenyl substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl,C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro,heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or bynitro, diheteroarylamino or diheteroarylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano ornitro, phenylamino or phenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,diphenylamino, or diphenylamino substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro,or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy,C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₈dialkylamino, benzyloxy orphenoxy, wherein the benzyl and phenyl groups may in turn be substitutedby C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen,cyano or nitro, andR^(h) is C₁-C₁₀alkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₁-C₁₀haloalkyl,C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₀aminoalkyl,C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl,C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl,C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl,C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl,C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₆alkyl,C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl,aminocarbonylC₁-C₅alkyl, C₁-C₈alkylaminocarbonylC₁-C₈alkyl,C₂-C₈dialkylaminocarbonylC₁-C₈alkyl, C₁-C₈alkylcarbonylaminoC₁-C₈alkyl,N—C₁-C₈alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₃alkyl,C₃-C₆trialkylsilylC₁-C₅alkyl, phenylC₁-C₅alkyl (wherein the phenyl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), heteroarylC₁-C₆alkyl(wherein the heteroaryl may optionally be substituted by C₁-C₃alkyl,C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio,C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro),phenoxyC₁-C₈alkyl (wherein the phenyl may optionally be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyanoor by nitro), heteroaryloxyC₁-C₈alkyl (wherein the heteroaryl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl,halogen, cyano or by nitro), C₃-C₅haloalkenyl, C₃-C₈cycloalkyl, phenylor phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, halogen or by nitro, or heteroaryl, or heteroarylsubstituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,halogen, cyano or by nitro.

In particular, the latentiating group G is a group —C(X^(a))—R^(a) or—C(X^(b))—X^(c)—R^(b), and the meanings of X^(a), R^(a), X^(b), X^(c),X^(b) and R^(b) are as defined above.

It is preferred that G is hydrogen, an alkali metal or alkaline earthmetal, where hydrogen is especially preferred.

It should be understood that in those compounds of formula I where G isa metal, ammonium (such as NH₄+; N(alkyl)₄+) or sulfonium (such asS(alkyl)₃+) cation, the corresponding negative charge is largelydelocalised across the O—C═C—C═O unit.

Depending on the nature of the substituents, compounds of formula I mayexist in different isomeric forms. When G is hydrogen, for example,compounds of formula I may exist in different tautomeric forms.

This invention covers all such isomers and tautomers and mixturesthereof in all proportions. Also, when substituents contain doublebonds, cis- and trans-isomers can exist. These isomers, too, are withinthe scope of the claimed compounds of the formula I.

A compound of formula I wherein G is C₁-C₈ alkyl, C₂-C₈ haloalkyl,phenylC₁-C₈alkyl (wherein the phenyl may optionally be substituted byC₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy,C₁-C₃alkylthio, C₁-C₃alkylsufinyl, C₁-C₃ alkylsulfonyl, halogen, cyanoor by nitro), heteroarylC₁-C₈alkyl (wherein the heteroaryl mayoptionally be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy,C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano or by nitro), C₃-C₈ alkenyl, C₃-C₈haloalkenyl, C₃-C₈ alkynyl, C(X^(a))—R^(a), C(X^(b))—X^(c)—R^(b),C(X^(d))—N(R^(c))—R^(d), —SO₂—R^(e), —P(X^(e))(R^(f))—R^(g) orCH₂—X^(f)—R^(h) where X^(a), X^(b), X^(c), X^(d), X^(e), X^(f), R^(a),R^(b), R^(c), R^(d), R^(e), R^(f), R^(g) and R^(h) are as defined abovemay be prepared by treating a compound of formula (A), which is acompound of formula I wherein G is H, with a reagent G-Z, wherein G-Z isalkylating agent such as an alkyl halide (the definition of alkylhalides includes simple C₁-C₈ alkyl halides such as methyl iodide andethyl iodide, substituted alkyl halides such as phenylC₁-C₆alkyl,chloromethyl alkyl ethers, Cl—CH₂—X^(f)—R^(h), wherein X^(f) is oxygen,and chloromethyl alkyl sulfides Cl—CH₂—X^(f)—R^(h), wherein X^(f) issulfur), a C₁-C₈ alkyl sulfonate, or a di-C₁-C₈-alkyl sulfate, or with aC₃-C₈ alkenyl halide, or with a C₃-C₈ alkynyl halide, or with anacylating agent such as a carboxylic acid, HO—C(X^(a))R^(a), whereinX^(a) is oxygen, an acid chloride, Cl—C(X^(a))R^(a), wherein X^(a) isoxygen, or acid anhydride, [R^(a)C(X^(a))]₂O, wherein X^(a) is oxygen,or an isocyanate, R^(c)N═C═O, or a carbamoyl chloride,Cl—C(X^(d))—-N(R^(c))—R^(d) (wherein X^(d) is oxygen and with theproviso that neither R^(c) or R^(d) is hydrogen), or a thiocarbamoylchloride, Cl—C(X^(d))—N(R^(d))—R^(d) (wherein X^(d) is sulfur and withthe proviso that neither R^(c) or R^(d) is hydrogen) or a chloroformate,Cl—C(X^(b))—X^(c)—R^(b), (wherein X^(b) and X^(c) are oxygen), or achlorothioformate Cl—C(X^(b))—X^(c)—R^(b) (wherein X^(b) is oxygen andX^(c) is sulfur), or a chlorodithioformate Cl—C(X^(b))—X^(c)—R^(b),(wherein X^(b) and X^(c) are sulfur), or an isothiocyanate, R^(c)N═C═S,or by sequential treatment with carbon disulfide and an alkylatingagent, or with a phosphorylating agent such as a phosphoryl chloride,Cl—P(X^(e))(R^(f))—R^(g) or with a sulfonylating agent such as asulfonyl chloride Cl—SO₂—R^(e), preferably in the presence of at leastone equivalent of base.

Depending on the nature of the substituents R¹ to R¹², and of the groupG, isomeric compounds of formula I may be formed. For example, acompound of formula (A) wherein R⁵ and R¹² are different may give riseto a compound of formula (1a) or to a compound of formula (1b), or to amixture of compounds of formula (1a) and formula (1b).

The O-alkylation of cyclic 1,3-diones is known; suitable methods aredescribed, for example, by T. Wheeler U.S. Pat. No. 4,436,666.Alternative procedures have been reported by M. Pizzorno and S.Albonico, Chem. Ind. (London), (1972), 425; H. Born et al., J. Chem.Soc., (1953), 1779; M. Constantino et al., Synth. Commun., (1992), 22(19), 2859; Y. Tian et al., Synth. Commun., (1997), 27 (9), 1577, S.Chandra Roy et al., Chem. Letters, (2006), 35 (1), 16, and P. Zubaidhaet al., Tetrahedron Lett., (2004), 45, 7187.

The O-acylation of cyclic 1,3-diones may be effected by proceduressimilar to those described, for example, by R. Haines, U.S. Pat. No.4,175,135, and by T. Wheeler, U.S. Pat. No. 4,422,870, U.S. Pat. No.4,659,372 and U.S. Pat. No. 4,436,666. Typically diones of formula (A)may be treated with the acylating agent in the presence of at least oneequivalent of a suitable base, optionally in the presence of a suitablesolvent. The base may be inorganic, such as an alkali metal carbonate orhydroxide, or a metal hydride, or an organic base such as a tertiaryamine or metal alkoxide. Examples of suitable inorganic bases includesodium carbonate, sodium or potassium hydroxide, sodium hydride, andsuitable organic bases include trialkylamines, such as trimethylamineand triethylamine, pyridines or other amine bases such as1,4-diazobicyclo[2.2.2]octane and 1,8-diazabicyclo[5.4.0]undec-7-ene.Preferred bases include triethylamine and pyridine. Suitable solventsfor this reaction are selected to be compatible with the reagents andinclude ethers such as tetrahydrofuran and 1,2-dimethoxyethane andhalogenated solvents such as dichloromethane and chloroform. Certainbases, such as pyridine and triethylamine, may be employed successfullyas both base and solvent. For cases where the acylating agent is acarboxylic acid, acylation is preferably effected in the presence of acoupling agent such as 2-chloro-1-methylpyridinium iodide, N,N′-dicyclohexylcarbodiimide,1-(3-dimethylaminopropyl)-3-ethylcarbodiimide and N,N′-carbodiimidazole,and optionally a base such as triethylamine or pyridine in a suitablesolvent such as tetrahydrofuran, dichloromethane or acetonitrile.Suitable procedures are described, for example, by W. Zhang and G. Pugh,Tetrahedron Lett., (1999), 40 (43), 7595-7598 and T. Isobe and T.Ishikawa, J. Org. Chem., (1999), 64 (19), 6984.

Phosphorylation of cyclic 1,3-diones may be effected using a phosphorylhalide or thiophosphoryl halide and a base by procedures analogous tothose described by L. Hodakowski, U.S. Pat. No. 4,409,153.

Sulfonylation of a compound of formula (A) may be achieved using analkyl or aryl sulfonyl halide, preferably in the presence of at leastone equivalent of base, for example by the procedure of C. Kowalski andK. Fields, J. Org. Chem., (1981), 46, 197.

A compound of formula (A) may be prepared by the cyclisation of acompound of formula (B), wherein R is hydrogen or an alkyl group,preferably in the presence of an acid or base, and optionally in thepresence of a suitable solvent, by analogous methods to those describedby T. Wheeler, U.S. Pat. No. 4,209,532. The compounds of formula (B)have been particularly designed as intermediates in the synthesis of thecompounds of the formula I. A compound of formula (B) wherein R ishydrogen may be cyclised under acidic conditions, preferably in thepresence of a strong acid such as sulfuric acid, polyphosphoric acid orEaton's reagent, optionally in the presence of a suitable solvent suchas acetic acid, toluene or dichloromethane.

A compound of formula (B) wherein R is alkyl (preferably methyl orethyl), may be cyclised under acidic or basic conditions, preferably inthe presence of at least one equivalent of a strong base such aspotassium tert-butoxide, lithium diisopropylamide or sodium hydride andin a solvent such as tetrahydrofuran, toluene, dimethylsulfoxide orN,N-dimethylformamide.

A compound of formula (B), wherein R is H, may be prepared bysaponification of a compound of formula (C) wherein R′ is alkyl(preferably methyl or ethyl), under standard conditions, followed byacidification of the reaction mixture to effect decarboxylation, bysimilar processes to those described, for example, by T. Wheeler, U.S.Pat. No. 4,209,532.

A compound of formula (B), wherein R is H, may be esterified to acompound of formula (B), wherein R is alkyl, under standard conditions,for example by heating with an alkyl alcohol, ROH, in the presence of anacid catalyst.

A compound of formula (C), wherein R is alkyl, may be prepared bytreating a compound of formula (D) with a suitable carboxylic acidchloride of formula (E) under basic conditions. Suitable bases includepotassium tert-butoxide, sodium bis(trimethylsilyl)amide and lithiumdiisopropylamide and the reaction is preferably conducted in a suitablesolvent (such as tetrahydrofuran or toluene) at a temperature of between−80° C. and 30° C. Alternatively, a compound of formula (C), wherein Ris H, may be prepared by treating a compound of formula (D) with asuitable base (such as potassium tert-butoxide, sodiumbis(trimethylsilyl)amide and lithium diisopropylamide) in a suitablesolvent (such as tetrahydrofuran or toluene) at a suitable temperature(between −80° C. and 30° C.) and reacting the resulting anion with asuitable anhydride of formula (F):

Compounds of formula (D) are known compounds, or may be prepared fromknown compounds by known methods.

A compound of formula (E) may be prepared from a compound of formula (F)by treatment with an alkyl alcohol, R—OH, in the presence of a base,such as dimethylaminopyridine or an alkaline metal alkoxide (see, forexample, S. Buser and A. Vasella, Helv. Chim. Acta, (2005), 88, 3151, M.Hart et al., Bioorg. Med. Chem. Letters, (2004), 14, 1969), followed bytreatment of the resulting acid with a chlorinating reagent such asoxalyl chloride or thionyl chloride under known conditions (see, forexample, C. Santelli-Rouvier. Tetrahedron Lett., (1984), 25 (39), 4371;D. Walba and M. Wand, Tetrahedron Lett., (1982), 23 (48), 4995; J.Cason, Org. Synth. Coll. Vol. III, (169), 1955).

A compound of formula (F) wherein R⁷ and R¹⁰ are hydrogen may beprepared by the reduction of a compound of formula (G) under knownconditions (see, for example, Y. Baba, N. Hirukawa and M. Sodeoka,Bioorg. Med. Chem. (2005), 13 (17), 5164, M. Hart et al., Bioorg. Med.Chem. Letters, (2004), 14 (18), 1969, Y. Baba, N. Hirukawa, N. Tanohiraand M. Sodeoka, J. Am. Chem. Soc., (2003), 125, 9740).

A compound of formula (G) may be prepared by reacting a compound offormula (H) with an anhydride of formula (J), optionally in the presenceof a Lewis acid catalyst, and according to procedures described, forexample, by O. Diels and K. Alder, Liebigs Ann. Chem., (1931), 490, 257,K. Potts and E. Walsh, J. Org. Chem., (1984), 49 (21), 4099, J. Jurczak,T. Kozluk, S. Filipek and S. Eugster, Helv. Chim. Acta, (1982), 65,1021, W. Dauben, C. Kessel and K. Takemura, J. Am. Chem. Soc., (1980),102, 6893, A. Pelter and B. Singaram, Tetrahedron Lett., (1982), 23,245, M. Lee and C. Hemdon, J. Org. Chem., (1978), 43, 518, B. Fisher andJ. Hodge, J. Org. Chem. (1964), 29, 776, G. D'Alelio, C. Williams and C.Wilson, J. Org. Chem., (1960), 25, 1028, Z. Song, M. Ho and H. Wong, J.Org. Chem., (1994), 59 (14), 3917-3926, W. Tochtermann, S. Bruhn and C.Wolff, Tetrahedron Lett., (1994), 35(8), 1165, W. Dauben, J. Lam and Z.Guo, J. Org. Chem., (1996), 61 (14), 4816, M. Sodeoka, Y. Baba, S.Kobayashi and N. Hirukawa, Bioorg. Med. Chem. Lett., (1997), 7 (14),1833, M. Avalos, R. Babiano, J. Bravo, P. Cintas, J. Jimenez and J.Palacios, Tetrahedron Lett., (1998), 39(50), 9301, J. Auge, R. Gil, S.Kalsey and N. Lubin-Germain, Synlett, (2000), 6, 877, I. Hemeon, C.Deamicis, H. Jenkins, P. Scammells and R. Singer, Synlett, (2002), 11,1815, M. Essers, B. Wibbeling and G. Haufe, Tetrahedron Lett., (2001),42 (32), 5429, P. Vogel et al., Tetrahedron Asymmetry, (1996), 7 (11),3153, Y. Baba, N. Hirukawa, N. Tanohira and M. Sodeoka, J. Am. Chem.Soc., (2003), 125, 9740, L. Ghosez et al., Tetrahedron Lett., (1988), 29(36), 4573, H. Kotsuki, S. Kitagawa and H. Nishizawa, J. Org. Chem.,(1978), 43 (7), 1471, Y. Li et al., J. Org. Chem., (1997), 62 (23),7926, M. Drew et al., J. Chem. Soc. Perkin Trans. 1, (1985), 1277, R.McDonald and C. Reineke, J. Org. Chem., (1967), 32, 1878, R. Fleming andB. Murray, J. Org. Chem., (1979), 44 (13), 2280, M. Goldstein and G.Thayer Jr. J. Am. Chem. Soc., (1965), 87 (9), 1925 and G. Keglevich etal., J. Organomet. Chem., (1999), 579, 182, and references therein.

-   -   Compounds of formula (H) and formula (J) are known compounds, or        may be made from known compounds by known methods.

Compounds of formula (G) are alkenes, and as such undergo furtherreactions typical of alkenes to give additional compounds of formula (F)according to known procedures. Examples of such reactions include, butare not restricted to, halogenation, epoxidation, cyclopropanation,dihydroxylation, hydroarylation, hydrovinylation and hydration ofalkenes. In turn, the products from these reactions may be transformedinto additional compounds of formula (F) by methods described, forexample by J. March, Advanced Organic Chemistry, third edition, JohnWiley and Sons. Compounds of formula (G) wherein R⁸ or R⁹ areC₁-C₆alkoxy are enol ethers, and these may be hydrolysed to thecorresponding ketone using standard procedures to give additionalcompounds of formula (F). Certain compounds of formula (F), for examplewhere R⁷ is a halogen, may be converted into compounds of formula (G) byknown methods.

A compound of formula (G) may also be prepared by reacting a compound offormula (H) with a compound of formula (K), wherein R″ is hydrogen or analkyl group, to give a compound of formula (L) and cyclising a compoundof formula (L) under known conditions (see, for example, P. Sprague etal., J. Med. Chem., (1985), 28, 1580, A. Guzaev and M. Manoharan, J. Am.Chem. Soc., (2003), 125, 2380, and A. Marchand and R. Allen, J. Org.Chem., (1975), 40 (17), 2551.

A compound of formula (L) may also be reduced to a compound of formula(M), and a compound of formula (M) cyclised to a compound of formula (F)wherein R⁷ and R¹⁰ are hydrogen, under conditions similar to thosedescribed previously.

Compounds of formula (K) are known compounds, or may be prepared fromknown compounds by known methods.

Additional compounds of formula (A) may be prepared by reacting aniodonium ylide of formula (N), wherein Ar is an optionally substitutedphenyl group, and an aryl boronic acid of formula (O), in the presenceof a suitable palladium catalyst, a base and in a suitable solvent.

Suitable palladium catalysts are generally palladium(II) or palladium(0)complexes, for example palladium(II)dihalides, palladium(II)acetate,palladium(II) sulfate, bis(triphenylphosphine)-palladium(II) dichloride,bis(tricyclopentylphosphine)palladium(II)dichloride,bis(tricyclohexyl-phosphine)palladium(II) dichloride,bis(dibenzylideneacetone)palladium(0) ortetrakis-(triphenylphosphine)palladium(0). The palladium catalyst canalso be prepared “in situ” from palladium(II) or palladium(0) compoundsby complexing with the desired ligands, by, for example, combining thepalladium(II) salt to be complexed, for example palladium(II)dichloride(PdCl₂) or palladium(II)acetate (Pd(OAc)₂), together with the desiredligand, for example triphenyl-phosphine (PPh₃), tricyclopentylphosphine,tricyclohexylphosphine, 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenylor 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl and theselected solvent, with a compound of formula (N), the arylboronic acidof formula (O), and a base. Also suitable are bidendate ligands, forexample 1,1′-bis(diphenylphosphino)ferrocene or1,2-bis(diphenylphosphino)ethane. By heating the reaction medium, thepalladium(II) complex or palladium(0) complex desired for the C—Ccoupling reaction is thus formed “in situ”, and then initiates the C—Ccoupling reaction.

The palladium catalysts are used in an amount of from 0.001 to 50 mol %,preferably in an amount of from 0.1 to 15 mol %, based on the compoundof formula (N). The reaction may also be carried out in the presence ofother additives, such as tetralkylammonium salts, for example,tetrabutylammonium bromide. Preferably the palladium catalyst ispalladium acetate, the base is lithium hydroxide and the solvent isaqueous 1,2-dimethoxyethane.

A compound of formula (N) may be prepared from a compound of formula (P)by treatment with a hypervalent iodine reagent such as a(diacetoxy)iodobenzene or an iodosylbenzene and a base such as aqueoussodium carbonate, lithium hydroxide or sodium hydroxide in a solventsuch as water or an aqueous alcohol such as aqueous ethanol according tothe procedures of K. Schank and C. Lick, Synthesis, (1983), 392, R. M.Moriarty et al., J. Am. Chem. Soc, (1985), 107, 1375, or of Z. Yang etal., Org. Lett., (2002), 4 (19), 3333.

A compound of formula (P) wherein R⁷ and R¹⁰ are hydrogen may beprepared by reduction of a compound of formula (Q) under knownconditions.

Compounds of formula (R) are alkenes, and as such undergo furtherreactions typical of alkenes to give additional compounds of formula (P)according to known procedures. Examples of such reactions include, butare not restricted to, halogenation, epoxidation, cyclopropanation,dihydroxylation, hydroarylation, hydrovinylation and hydration ofalkenes. In turn, the products of these reactions may be transformedinto additional compounds of formula (P) by methods described, forexample by J. March, Advanced Organic Chemistry, third edition, JohnWiley and Sons. Compounds of formula (R) wherein R⁸ or R⁹ areC₁-C₆alkoxy are enol ethers, and these may be hydrolysed to thecorresponding ketone using standard procedures. In turn, the ketone maybe further transformed, for example by ketalisation, oximation,reduction and the like under known conditions to give additionalcompounds of formula (P).

A compound of formula (R) may be prepared by reacting a compound offormula (S) with a cyclopentenedione of formula (T), optionally in thepresence of a Lewis acid catalyst, according to procedures described,for example by B. Zwanenburg et al., Tetrahedron (1989), 45 (22), 7109and by M. Oda et al., Chem. Lett., (1977), 307.

Compounds of formula (H) and formula (T) are known compounds or may bemade from known compounds by known methods.

In a further approach, a compound of formula (A) may be prepared from acompound of formula I, wherein G is C₁₋₄ alkyl, by hydrolysis,preferably in the presence of an acid catalyst such as hydrochloric acidand optionally in the presence of a suitable solvent such astetrahydrofuran, acetone or 4-methylpentan-2-one.

A compound of formula I wherein G is C₁₋₄ alkyl, may be prepared from acompound of formula (U), wherein G is C₁₋₄ alkyl, and Hal is a halogen(preferably bromine or iodine), by coupling with an aryl boronic acid offormula (O), in the presence of a suitable palladium catalyst and a baseand preferably in the presence of a suitable ligand, and in a suitablesolvent. Preferably the palladium catalyst is palladium acetate, thebase is potassium phosphate, the ligand is2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl and the solvent istoluene.

A compound of formula (U) may be prepared by halogenation of a compoundof formula (P), followed by reaction of the resulting halide of formula(V) with a C₁₋₄ alkyl halide or tri-C₁₋₄-alkylorthoformate under knownconditions (for example by the procedures of R. Shepherd and A. White,J. Chem. Soc. Perkin Trans. 1 (1987), 2153, and Y.-L. Lin et at.,Bioorg. Med. Chem. (2002), 10, 685). Alternatively, a compound offormula (U) may be prepared by reaction of a compound of formula (P)with a C₁₋₄ alkyl halide or a tri-C₁₋₄-alkylorthoformate, andhalogenation of the resulting enone of formula (W) under knownconditions.

A compound of formula (O) may be prepared from an aryl halide of formula(X), wherein Hal is bromine or iodine, by known methods (see, forexample, W. Thompson and J. Gaudino, J. Org. Chem., (1984), 49, 5237 andR. Hawkins et al., J. Am. Chem. Soc., (1960), 82, 3053). For example, anaryl halide of formula (X) may be treated with an alkyl lithium or alkylmagnesium halide in a suitable solvent, preferably diethyl ether ortetrahydrofuran, at a temperature of between −80° C. and 30° C., and thearyl magnesium or aryl lithium reagent obtained may then be reacted witha trialkyl borate (preferably trimethylborate) to give an aryldialkylboronate which may be hydrolysed to provide a boronic acid offormula (O) under acidic conditions.

Alternatively a compound of formula (X) may be reacted with a cyclicboronate ester derived from a 1,2- or a 1,3-alkanediol such as pinacol,2,2-dimethyl-1,3-propanediol and 2-methyl-2,4-pentanediol) under knownconditions (see, for example, N. Miyaura et al., J. Org. Chem., (1995),60, 7508, and W. Zhu and D. Ma, Org. Lett., (2006), 8 (2), 261), and theresulting boronate ester may be hydrolysed under acidic conditions togive a boronic acid of formula (O). An aryl halide of formula (X) may beprepared from an aniline of formula (Y) by known methods, for examplethe Sandmeyer reaction, via the corresponding diazonium salts. Anilinesof formula (Y) are known compounds, or may be made from known compounds,by known methods.

Additional compounds of formula (A) may be prepared by reacting acompound of formula (P), or a compound of formula (R) with an organoleadreagent of formula (Z) under conditions described, for example, by J.Pinhey, Pure and Appl. Chem., (1996), 68 (4), 819 and by M. Moloney etal., Tetrahedron Lett., (2002), 43, 3407.

The organolead reagent of formula (Z) may be prepared from a boronicacid of formula (O), a stannane of formula (AA), wherein R is C₁-C₄alkyl or by direct plumbation of a compound of formula (AB) with leadtetraacetate according to known procedures.

Further compounds of formula (A) may be prepared by reacting a compoundof formula (P) or a compound of formula (R) with suitable triarylbismuthcompound under conditions described, for example, by A. Yu. Fedorov etal., Russ. Chem. Bull. Int. Ed., (2005), 54 (11), 2602, and by P. Koechand M. Krische, J. Am. Chem. Soc., (2004), 126 (17), 5350 and referencestherein.

In a further approach, a compound of formula I may be prepared from acompound of formula (AC) by suitable derivatisation under standardconditions.

For example, compounds of formula (AC) are alkenes, and as such undergofurther reactions typical of alkenes to give compounds of formula Iaccording to known procedures. Examples of such reactions include, butare not restricted to, reduction, halogenation, epoxidation,cyclopropanation, dihydroxylation, hydroarylation, hydrovinylation andhydration. Compounds of formula (AC) wherein R⁸ or R⁹ is bromine oriodine are vinyl halides, and undergo known reactions of vinyl halidessuch as Suzuki-Miyaura, Sonogashira, Stille and related reactions.Certain other compounds of formula (AC), wherein R⁸ or R⁹ isC₁-C₆alkoxy, are enol ethers, and these may be hydrolysed to thecorresponding ketone using standard procedures. In turn, the ketoneproduced may be further transformed, for example by ketalisation,oximation, reduction and the like under known conditions to giveadditional compounds of formula I. Similarly, compounds of formula (AC)wherein R⁸ or R⁹ is C₁-C₆amino or di-C₁-C₆amino are enamines, and thesealso may be hydrolysed to the corresponding ketone using standardprocedures.

A compound of formula (AC), wherein G is C₁-C₄ alkyl, may be preparedfrom a compound of formula (AD), wherein G is C₁-C₄ alkyl and X ishalogen or other suitable leaving group (such as an alkyl orarylsulfonate, or an arylselenoxide), by reaction with a compound offormula (I-1), optionally in a suitable solvent, and optionally in thepresence of a suitable base.

Suitable solvents include toluene, dichloromethane and chloroform andsuitable bases include organic bases such as triethylamine, Hunig's baseand 1,8-diazabicyclo[5.4.0]undec-7-ene. Preferably the solvent istoluene and the base is 1,8-diazabicyclo[5.4.0]undec-7-ene.

A compound of formula (AD) may be prepared from a compound of formula(AE), under known conditions.

For example, a compound of formula (AD) wherein X is chlorine may beprepared by reacting a compound of formula (AE) with copper(II) chlorideand lithium chloride according to the procedure of E. Kosower et al., J.Org. Chem., (1963), 28, 630.

Compounds of formula (AE) are known compounds or may be made from knowncompounds by known methods (see, for example, Y. Song, B. Kim and J-NHeo, Tetrahedron Lett., (2005), 46, 5977). Alternatively, a compound offormula (AE) wherein G is C₁-C₄alkyl may be prepared from a compound offormula (AE), wherein G is hydrogen, for example by reaction with a C₁₋₄alkyl halide or a tri-C₁₋₄-alkylorthoformate. Compounds of formula (AE),wherein G is hydrogen, are known, or may be prepared from knowncompounds by known methods (see, for example, T. Wheeler, U.S. Pat. No.4,338,122, U.S. Pat. No. 4,283,348, J. T. Kuethe et al., J. Org. Chem.,(2002), 67, 5993, S. Buchwald et al., J. Am. Chem. Soc., (2003), 125,11818).

Alternatively, a compound of formula (AE), wherein G is C₁₋₄alkyl, maybe prepared by reacting a compound of formula (AF), wherein G isC₁₋₄alkyl and Z is a halogen, preferably bromine or iodine, with aboronic acid of formula (O) in the presence of a suitable metalcatalyst, a suitable base, and optionally a suitable ligand, in asuitable solvent.

Suitable solvents include toluene and n-butanol, suitable bases includeinorganic bases such as potassium phosphate, a suitable metal catalystis a palladium catalyst, for example in the form ofpalladium(II)acetate, and suitable ligands include substitutedphosphines, for example 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl.

Compounds of formula (AF) are known compounds, or may be prepared bymethods known in the literature. For example a compound of formula (AF)wherein G is C₁₋₄alkyl and Z is a bromine atom may be prepared byreacting a compound of formula (AG), wherein G is C₁₋₄alkyl, with asuitable brominating agent, such as N-bromosuccinimide, in a suitablesolvent, such as 1,2-dichloroethane, as described by R. Shepherd and A.White, J. Chem. Soc. Perkin Trans. 1 (1987), 10, 2153.

In a similar manner, a compound of formula (A) may be prepared from acompound of formula (AH) by suitable derivatisation under standardconditions.

For example, compounds of formula (AH) are alkenes, and as such undergofurther reactions typical of alkenes to give compounds of formula (A)according to known procedures. Examples of such reactions include, butare not restricted to, reduction, halogenation, epoxidation,cyclopropanation, dihydroxylation, hydroarylation, hydrovinylation andhydration. Compounds of formula (AH) wherein R⁸ or R⁹ is bromine oriodine are vinyl halides, and undergo known reactions of vinyl halidessuch as Suzuki-Miyaura, Sonogashira, Stille and related reactions.Certain other compounds of formula (AH), wherein R⁸ or R⁹ isC₁-C₆alkoxy, are enol ethers, and these may be hydrolysed to thecorresponding ketone using standard procedures. In turn, the ketoneproduced may be further transformed, for example by ketalisation,oximation, reduction and the like under known conditions to giveadditional compounds of formula (A). Similarly, compounds of formula(AH) wherein R⁸ or R⁹ is C₁-C₆amino or di-C₁-C₆amino are enamines, andthese also may be hydrolysed to the corresponding ketone using standardprocedures.

A compound of formula (AH) may be prepared from a compound of formula(AI) by reaction with a compound of formula (H), optionally in asuitable solvent, and optionally in the presence of a suitable catalyst.The compounds of formula (AI) have been particularly designed asintermediates in the synthesis of the compounds of the formula I.

Compounds of the formula (AI) having the specific formulae

are known under the CAS registry numbers 299968-82-4 and 528833-96-7,respectively.

Preferably the catalyst is a Lewis acid catalyst such as aluminiumchloride, bismuth (III) chloride, bismuth (III)trifluoromethanesulfonate, boron trifluoride, cerium (III) chloride,copper (I) trifluoromethanesulfonate, diethylaluminium chloride, hafnium(IV) chloride, iron (III) chloride, lithium perchlorate, lithiumtrifluoromethanesulfonate, magnesium bromide, magnesium iodide, scandium(III) trifluoromethanesulfonate, tin (IV) chloride, titanium (IV)chloride, titanium (IV) isopropoxide, trimethyl aluminium,N-trimethylsilyl-bis(trifluoromethanesulfonyl)imide, trimethylsilyltrifluoromethane-sulfonate, ytterbium (III) trifluoromethanesulfonate,zinc iodide and zirconium (IV) chloride. Magnesium iodide isparticularly preferred. Suitable solvents include those which are knownto be effective solvents for conducting Diels-Alder reactions, amongthem, for example, chloroform, dichloromethane, diethyl ether, ethanol,methanol, perfluorinated alkanes, such as perfluorohexane, toluene,water, and ionic liquids such as 1-butyl-3-methylimidazoliumtetrafluoroborate and 1-butyl-3-methylimidazolium hexafluorophosphate.Dichloromethane is particularly preferred as a solvent.

A compound of formula (AI), may be prepared by oxidising a compound offormula (AJ) in a suitable solvent such as toluene, acetone, chloroform,dichloromethane or 1,4-dioxane. A wide range of oxidants are suitablefor effecting this transformation, including inorganic oxidants such aschromium trioxide, pyridinium dichromate, manganese dioxide andaluminium alkoxides such as aluminium isopropoxide, as well as organicoxidants such as 2,3-dichloro-5,6-dicyano-p-benzoquinone and hypervalentiodine oxidants such as1,1,1,-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one(Dess-Martin periodinane), Suitable procedures are described, forexample, by K. Saito and H. Yamachika, U.S. Pat. No. 4,371,711. and byG. Piancatelli et al., Tetrahedron (1978), 34, 2775. The use of chromiumtrioxide in a mixture of sulfuric acid and acetone (Jones reagent) ispreferred.

The compounds of the formula AI have been particularly designed asintermediates for the synthesis of the compounds of the formula I.

Particularly useful compounds of the formula AI are those, wherein R⁵and R¹² are hydrogen.

In another group of useful compounds of the formula I, R¹, R² and R⁴ areindependently of each other methyl or ethyl.

In another group of useful compounds of the formula I, R¹, R² and R⁴ areindependently of each other methyl or ethyl, and R³, R⁵ and R¹² arehydrogen.

A compound of formula (AJ) may be prepared from a compound of formula(AK) by treatment with a suitable acid catalyst in the presence of waterand optionally in the presence of a suitable solvent, according to knownprocedures.

For example, a compound of formula (AK) may be converted to a compoundof formula (AJ) in the presence of an aqueous solution of an acid suchas phosphoric acid or polyphosphoric acid as described, for example byK. Saito and H. Yamachika, U.S. Pat. No. 4,371,711. Alternatively acompound of formula (AJ) may be prepared from a compound of formula (AK)by rearrangement in the presence of a Lewis acid catalyst such as zincchloride according to the procedure of G. Piancatelli et al.,Tetrahedron, (1978), 34, 2775.

A compound of formula (AK) may be prepared by the reduction of acompound of formula (AL) by known conditions (see, for example RSilvestri et al., J. Med. Chem., 2005, 48, 4378-4388).

Compounds of formula (AL) are known, or may be made by known methodsfrom known compounds (see, for example, L. Liebeskind et al., Org.Lett., (2003), 5 (17), 3033-3035, H. Firouzabadi, N. Iranpoor and F.Nowrouzi, Tetrahedron, (2004), 60,10843, R. Silvestri et al., J. Med.Chem., (2005), 48, 4378 and references therein).

Alternatively a compound of formula (AK) may be prepared by the additionof a suitable organometallic reagent such as an arylmagnesium halide offormula (AM) wherein Hal is a halide such as chloride, bromide oriodide, or an aryllithium reagent of formula (AN) or a diarylzincreagent of formula (AO) to a furan-2-carboxaldehyde of formula (AP)according to known procedures (see, for example G. Panda et al.,Tetrahedron Lett., (2005), 46, 3097).

Additional compounds of formula (AK) may be prepared from compounds offormula (AR) by reaction with a strong base, for a example an alkyllithium reagent such as n-butyllithium, optionally in the presence of anadditive such as tetramethylethylenediamine, and in a suitable solventsuch as diethyl ether or tetrahydrofuran, followed by reaction with abenzaldehyde of formula (AS) as described, for example by I. Gupta andM. Ravikanth, J. Org. Chem., (2004), 69, 6796, A. M. Echavarren et al.,J. Am. Chem. Soc., (2003), 125 (19), 5757, and by T. K. Chandrashekar etal., J. Org. Chem., (2002), 67, 6309-6319.

The organometallic reagents of formula (AM), formula (AN) and formula(AO) are known compounds or may be made by known methods from knowncompounds. Compounds of formula (AP), formula (AR) and formula (AS) areknown compounds, or may be prepared from known compounds by knownmethods.

The compounds of formula I according to the invention can be used asherbicides in unmodified form, as obtained in the synthesis, but theyare generally formulated into herbicidal compositions in a variety ofways using formulation adjuvants, such as carriers, solvents andsurface-active substances. The formulations can be in various physicalforms, for example in the form of dusting powders, gels, wettablepowders, water-dispersible granules, water-dispersible tablets,effervescent compressed tablets, emulsifiable concentrates,microemulsifiable concentrates, oil-in-water emulsions, oil flowables,aqueous dispersions, oily dispersions, suspoemulsions, capsulesuspensions, emulsifiable granules, soluble liquids, water-solubleconcentrates (with water or a water-miscible organic solvent ascarrier), impregnated polymer films or in other forms known, forexample, from the Manual on Development and Use of FAO Specificationsfor Plant Protection Products, 5th Edition, 1999. Such formulations caneither be used directly or are diluted prior to use. Dilutedformulations can be prepared, for example, with water, liquidfertilisers, micronutrients, biological organisms, oil or solvents.

The formulations can be prepared, for example, by mixing the activeingredient with formulation adjuvants in order to obtain compositions inthe form of finely divided solids, granules, solutions, dispersions oremulsions. The active ingredients can also be formulated with otheradjuvants, for example finely divided solids, mineral oils, vegetableoils, modified vegetable oils, organic solvents, water, surface-activesubstances or combinations thereof. The active ingredients can also becontained in very fine microcapsules consisting of a polymer.Microcapsules contain the active ingredients in a porous carrier. Thisenables the active ingredients to be released into their surroundings incontrolled amounts (e.g. slow release). Microcapsules usually have adiameter of from 0.1 to 500 microns. They contain active ingredients inan amount of about from 25 to 95% by weight of the capsule weight. Theactive ingredients can be present in the form of a monolithic solid, inthe form of fine particles in solid or liquid dispersion or in the formof a suitable solution. The encapsulating membranes comprise, forexample, natural and synthetic gums, cellulose, styrene-butadienecopolymers, polyacrylonitrile, polyacrylate, polyester, polyamides,polyureas, polyurethane or chemically modified polymers and starchxanthates or other polymers that are known to the person skilled in theart in this connection. Alternatively it is possible for very finemicrocapsules to be formed wherein the active ingredient is present inthe form of finely divided particles in a solid matrix of a basesubstance, but in that case the microcapsule is not encapsulated.

The formulation adjuvants suitable for the preparation of thecompositions according to the invention are known per se. As liquidcarriers there may be used: water, toluene, xylene, petroleum ether,vegetable oils, acetone, methyl ethyl ketone, cyclohexanone, acidanhydrides, acetonitrile, acetophenone, amyl acetate, 2-butanone,butylenes carbonate, chlorobenzene, cyclohexane, cyclohexanol, alkylesters of acetic acid, diacetone alcohol, 1,2-dichloropropane,diethanolamine, p-diethylbenzene, diethylene glycol, diethylene glycolabietate, diethylene glycol butyl ether, diethylene glycol ethyl ether,diethylene glycol methyl ether, N,N-dimethylformamide, dimethylsulfoxide, 1,4-dioxane, dipropylene glycol, dipropylene glycol methylether, dipropylene glycol dibenzoate, diproxitol, alkylpyrrolidone,ethyl acetate, 2-ethyl hexanol, ethylene carbonate,1,1,1-trichloroethane, 2-heptanone, alpha-pinene, d-limonene, ethyllactate, ethylene glycol, ethylene glycol butyl ether, ethylene glycolmethyl ether, gamma-butyrolactone, glycerol, glycerol acetate, glyceroldiacetate, glycerol triacetate, hexadecane, hexylene glycol, isoamylacetate, isobornyl acetate, isooctane, isophorone, isopropylbenzene,isopropyl myristate, lactic acid, laurylamine, mesityl oxide,methoxypropanol, methyl isoamyl ketone, methyl isobutyl ketone, methyllaurate, methyl octanoate, methyl oleate, methylene chloride, m-xylene,n-hexane, n-octylamine, octadecanoic acid, octylamine acetate, oleicacid, oleylamine, o-xylene, phenol, polyethylene glycol (PEG 400),propionic acid, propyl lactate, propylene carbonate, propylene glycol,propylene glycol methyl ether, p-xylene, toluene, triethyl phosphate,triethylene glycol, xylenesulfonic acid, paraffin, mineral oil,trichloroethylene, perchloroethylene, ethyl acetate, amyl acetate, butylacetate, propylene glycol methyl ether, diethylene glycol methyl ether,methanol, ethanol, isopropanol, and higher molecular weight alcohols,such as amyl alcohol, tetrahydrofurfuryl alcohol, hexanol, octanol,ethylene glycol, propylene glycol, glycerol, N-methyl-2-pyrrolidone andthe like. Water is generally the carrier of choice for the dilution ofthe concentrates. Suitable solid carriers are, for example, talc,titanium dioxide, pyrophyllite clay, silica, attapulgite clay,kieselguhr, limestone, calcium carbonate, bentonite, calciummontomorillonite, cottonseed husks, wheatmeal, soybean flour, pumice,wood flour, ground walnut shells, lignin and similar materials, asdescribed, for example, in CFR 180.1001. (c) & (d).

A large number of surface-active substances can advantageously be usedboth in solid and in liquid formulations, especially in thoseformulations which can be diluted with a carrier prior to use.Surface-active substances may be anionic, cationic, non-ionic orpolymeric and they may be used as emulsifying, wetting or suspendingagents or for other purposes. Typical surface-active substances include,for example, salts of alkyl sulfates, such as diethanolammonium laurylsulfate; salts of alkylarylsulfonates, such as calciumdodecylbenzenesulfonate; alkylphenol-alkylene oxide addition products,such as nonylphenol ethoxylate; alcohol-alkylene oxide additionproducts, such as tridecyl alcohol ethoxylate; soaps, such as sodiumstearate; salts of alkylnaphthalenesulfonates, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl)sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride, polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono- and di-alkyl phosphate esters; andalso further substances described e.g. in “McCutcheon's Detergents andEmulsifiers Annual”, MC Publishing Corp., Ridgewood, N.J., 1981.

Further adjuvants which can usually be used in pesticidal formulationsinclude crystallisation inhibitors, viscosity-modifying substances,suspending agents, dyes, anti-oxidants, foaming agents, light absorbers,mixing aids, anti-foams, complexing agents, neutralising or pH-modifyingsubstances and buffers, corrosion-inhibitors, fragrances, wettingagents, absorption improvers, micronutrients, plasticisers, glidants,lubricants, dispersants, thickeners, anti-freezes, microbiocides, andalso liquid and solid fertilisers.

The formulations may also comprise additional active substances, forexample further herbicides, herbicide safeners, plant growth regulators,fungicides or insecticides.

The compositions according to the invention can additionally include anadditive comprising an oil of vegetable or animal origin, a mineral oil,alkyl esters of such oils or mixtures of such oils and oil derivatives.The amount of oil additive used in the composition according to theinvention is generally from 0.01 to 10%, based on the spray mixture. Forexample, the oil additive can be added to the spray tank in the desiredconcentration after the spray mixture has been prepared. Preferred oiladditives comprise mineral oils or an oil of vegetable origin, forexample rapeseed oil, olive oil or sunflower oil, emulsified vegetableoil, such as AMIGO® (Rhone-Poulenc Canada Inc.), alkyl esters of oils ofvegetable origin, for example the methyl derivatives, or an oil ofanimal origin, such as fish oil or beef tallow. A preferred additivecontains, for example, as active components essentially 80% by weightalkyl esters of fish oils and 15% by weight methylated rapeseed oil, andalso 5% by weight of customary emulsifiers and pH modifiers. Especiallypreferred oil additives comprise alkyl esters of C₈-C₂₂ fatty acids,especially the methyl derivatives of C₁₂-C₁₈ fatty acids, for examplethe methyl esters of lauric acid, palmitic acid and oleic acid, beingimportant. Those esters are known as methyl laurate (CAS-111-82-0),methyl palmitate (CAS-112-39-0) and methyl oleate (CAS-112-62-9). Apreferred fatty acid methyl ester derivative is Emery® 2230 and 2231(Cognis GmbH). Those and other oil derivatives are also known from theCompendium of Herbicide Adjuvants, 5th Edition, Southern IllinoisUniversity, 2000.

The application and action of the oil additives can be further improvedby combining them with surface-active substances, such as non-ionic,anionic or cationic surfactants. Examples of suitable anionic, non-ionicand cationic surfactants are listed on pages 7 and 8 of WO 97/34485.Preferred surface-active substances are anionic surfactants of thedodecylbenzylsulfonate type, especially the calcium salts thereof, andalso non-ionic surfactants of the fatty alcohol ethoxylate type. Specialpreference is given to ethoxylated C₁₂-C₂₂ fatty alcohols having adegree of ethoxylation of from 5 to 40. Examples of commerciallyavailable surfactants are the Genapol types (Clariant AG). Alsopreferred are silicone surfactants, especially polyalkyl-oxide-modifiedheptamethyltrisiloxanes, which are commercially available e.g. as SilwetL-77®, and also perfluorinated surfactants. The concentration ofsurface-active substances in relation to the total additive is generallyfrom 1 to 30% by weight. Examples of oil additives that consist ofmixtures of oils or mineral oils or derivatives thereof with surfactantsare Edenor ME SU®, Turbocharge® (Syngenta AG, CH) and Actipron® (BP OilUK Limited, GB).

The said surface-active substances may also be used in the formulationsalone, that is to say without oil additives.

Furthermore, the addition of an organic solvent to the oiladditive/surfactant mixture can contribute to a further enhancement ofaction. Suitable solvents are, for example, Solvesso® (ESSO) andAromatic Solvent® (Exxon Corporation). The concentration of suchsolvents can be from 10 to 80% by weight of the total weight. Such oiladditives, which may be in admixture with solvents, are described, forexample, in U.S. Pat. No. 4,834,908. A commercially available oiladditive disclosed therein is known by the name MERGE® (BASFCorporation). Further oil additives that are preferred according to theinvention are SCORE® (Syngenta Crop Protection Canada) and Adigor®(Syngenta Crop Protection Canada).

In addition to the oil additives listed above, in order to enhance theactivity of the compositions according to the invention it is alsopossible for formulations of alkylpyrrolidones, (e.g. Agrimax®) to beadded to the spray mixture. Formulations of synthetic latices, such as,for example, polyacrylamide, polyvinyl compounds or poly-1-p-menthene(e.g. Bond®, Courier® or Emerald®) can also be used. Solutions thatcontain propionic acid, for example Eurogkem Pen-e-trate®, can also bemixed into the spray mixture as activity-enhancing agents.

The herbicidal formulations generally contain from 0.1 to 99% by weight,especially from 0.1 to 95% by weight, of a compound of formula I andfrom 1 to 99.9% by weight of a formulation adjuvant, which preferablyincludes from 0 to 25% by weight of a surface-active substance. Whereascommercial products will preferably be formulated as concentrates, theend user will normally employ dilute formulations.

The rate of application of the compounds of formula I may vary withinwide limits and depends upon the nature of the soil, the method ofapplication (pre- or post-emergence; seed dressing; application to theseed furrow; no tillage application etc.), the crop plant, the weed orgrass to be controlled, the prevailing climatic conditions, and otherfactors governed by the method of application, the time of applicationand the target crop. The compounds of formula I according to theinvention are generally applied at a rate of 1-2000 g/ha, preferably1-1000 g/ha and most preferably at 1-500 g/ha.

Preferred formulations have especially the following compositions:Emulsifiable concentrates: active ingredient: 1 to 95%, preferably 60 to90% surface-active agent: 1 to 30%, preferably  5 to 20% liquid carrier:1 to 80%, preferably  1 to 35% Dusts: active ingredient:  0.1 to 10%,preferably  0.1 to 5% solid carrier: 99.9 to 90%, preferably 99.9 to 99%Suspension concentrates: active ingredient:  5 to 75%, preferably 10 to50% water: 94 to 24%, preferably 88 to 30% surface-active agent:  1 to40%, preferably  2 to 30% Wettable powders: active ingredient: 0.5 to90%, preferably  1 to 80% surface-active agent: 0.5 to 20%, preferably 1 to 15% solid carrier:   5 to 95%, preferably 15 to 90% Granules:active ingredient:  0.1 to 30%, preferably 0.1 to 15% solid carrier:99.5 to 70%, preferably  97 to 85% (% = percent by weight):

The following Examples further illustrate, but do not limit, theinvention.

F1. Emulsifiable concentrates a) b) c) d) active ingredient 5% 10% 25%50% calcium dodecylbenzene- 6%  8%  6% 8% sulfonate castor oilpolyglycol ether 4% —  4% 4% (36 mol of ethylene oxide) octylphenolpolyglycol ether —  4% — 2% (7-8 mol of ethylene oxide) NMP — — 10% 20%arom. hydrocarbon 85%  78% 55% 16% mixture C₉-C₁₂

Emulsions of any desired concentration can be prepared from suchconcentrates by dilution with water.

F2. Solutions a) b) c) d) active ingredient  5% 10% 50% 90%1-methoxy-3-(3-methoxy- — 20% 20% — propoxy)-propane polyethylene glycolMW 400 20% 10% — — NMP — — 30% 10% arom. hydrocarbon 75% 60% — — mixtureC₉-C₁₂

The solutions are suitable for application in the form of microdrops.

F3. Wettable powders a) b) c) d) active ingredient 5% 25%  50%  80%sodium lignosulfonate 4% — 3% — sodium lauryl sulfate 2% 3% —  4% sodiumdiisobutylnaphthalene- — 6% 5%  6% sulfonate octylphenol polyglycolether — 1% 2% — (7-8 mol of ethylene oxide) highly disperse silicic acid1% 3% 5% 10% kaolin 88%  62%  35%  —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, yielding wettablepowders which can be diluted with water to give suspensions of anydesired concentration.

F4. Coated granules a) b) c) active ingredient 0.1% 5% 15% highlydisperse silicic acid 0.9% 2% 2% inorg. carrier 99.0% 93% 83% (diameter0.1-1 mm)e.g. CaCO₃ or SiO₂

The active ingredient is dissolved in methylene chloride, the solutionis sprayed onto the carrier and the solvent is subsequently evaporatedoff in vacuo.

F5. Coated granules a) b) c) active ingredient 0.1% 5% 15% polyethyleneglycol MW 200 1.0% 2% 3% highly disperse silicic acid 0.9% 1% 2% inorg.carrier 98.0% 92% 80% (diameter 0.1-1 mm)e.g. CaCO₃ or SiO₂

The finely ground active ingredient is applied uniformly, in a mixer, tothe carrier moistened with polyethylene glycol. Non-dusty coatedgranules are obtained in this manner.

F6. Extruder granules a) b) c) d) active ingredient 0.1% 3% 5% 15%sodium lignosulfonate 1.5% 2% 3% 4% carboxymethylcellulose 1.4% 2% 2% 2%kaolin 97.0% 93% 90% 79%

The active ingredient is mixed and ground with the adjuvants and themixture is moistened with water. The resulting mixture is extruded andthen dried in a stream of air.

F7. Dusts a) b) c) active ingredient 0.1% 1% 5% talcum 39.9% 49% 35%kaolin 60.0% 50% 60%

Ready-to-use dusts are obtained by mixing the active ingredient with thecarriers and grinding the mixture in a suitable mill.

F8. Suspension concentrates a) b) c) d) active ingredient 3% 10%  25% 50%  ethylene glycol 5% 5% 5% 5% nonylphenol polyglycol ether — 1% 2% —(15 mol of ethylene oxide) sodium lignosulfonate 3% 3% 4% 5%carboxymethylcellulose 1% 1% 1% 1% 37% aqueous formaldehyde 0.2%  0.2%   0.2%   0.2%   solution silicone oil emulsion 0.8%   0.8%   0.8%  0.8%   water 87%  79%  62%  38% 

The finely ground active ingredient is intimately mixed with theadjuvants, yielding a suspension concentrate from which suspensions ofany desired concentration can be prepared by dilution with water.

The invention relates also to a method for the selective control ofgrasses and weeds in crops of useful plants, and for non-selective weedcontrol, which comprises treating the useful plants or the area undercultivation or the locus thereof with a compound of formula I.

Crops of useful plants in which the compositions according to theinvention can be used include especially cereals, in particular wheatand barley, rice, corn, rape, sugarbeet, sugarcane, soybean, cotton,sunflower, peanut and plantation crops.

The term “crops” is to be understood as also including crops that havebeen rendered tolerant to herbicides or classes of herbicides (forexample ALS, GS, EPSPS, PPO and HPPD inhibitors) as a result ofconventional methods of breeding or genetic engineering. An example of acrop that has been rendered tolerant e.g. to imidazolinones, such asimazamox, by conventional methods of breeding is Clearfield® summer rape(Canola). Examples of crops that have been rendered tolerant toherbicides by genetic engineering methods include e.g. glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady® and LibertyLink®. The weeds to be controlledmay be both monocotyledonous and dicotyledonous weeds, such as, forexample, Stellaria, Nasturtium, Agrostis, Digitaria, Avena, Setaria,Sinapis, Lolium, Solanum, Echinochloa, Scirpus, Monochoria, Sagittaria,Bromus, Alopecurus, Sorghum, Rottboellia, Cyperus, Abutilon, Sida,Xanthium, Amaranthus, Chenopodium, Ipomoea, Chrysanthemum, Galium, Violaand Veronica. Control of monocotyledonous weeds, in particular Agrostis,Avena, Setaria, Lolium, Echinochloa, Bromus, Alopecurus and Sorghum isvery extensive.

Crops are also to be understood as being those which have been renderedresistant to harmful insects by genetic engineering methods, for exampleBt maize (resistant to European corn borer), Bt cotton (resistant tocotton boll weevil) and also Bt potatoes (resistant to Colorado beetle).Examples of Bt maize are the Bt-176 maize hybrids of NK® (SyngentaSeeds). The Bt toxin is a protein that is formed naturally by Bacillusthuringiensis soil bacteria. Examples of toxins and transgenic plantsable to synthesise such toxins are described in EP-A-451 878, EP-A-374753, WO 93/07278, WO 95/34656, WO 03/052073 and EP-A-427 529. Examplesof transgenic plants that contain one or more genes which code for aninsecticidal resistance and express one or more toxins are KnockOut®(maize), Yield Gard® (maize), NuCOTIN33B® (cotton), Bollgard® (cotton),NewLeaf® (potatoes), NatureGard® and Protexcta®. Plant crops and theirseed material can be resistant to herbicides and at the same time alsoto insect feeding (“stacked” transgenic events). Seed can, for example,have the ability to express an insecticidally active Cry3 protein and atthe same time be glyphosate-tolerant. The term “crops” is to beunderstood as also including crops obtained as a result of conventionalmethods of breeding or genetic engineering which contain so-calledoutput traits (e.g. improved flavour, storage stability, nutritionalcontent).

Areas under cultivation are to be understood as including land where thecrop plants are already growing as well as land intended for thecultivation of those crop plants.

The compounds of formula I according to the invention can also be usedin combination with further herbicides. Preferably, in these mixtures,the compound of the formula I is one of those compounds listed in Tables1 to 146 below. The following mixtures of the compound of formula I areespecially important:

compound of formula I+acetochlor, compound of formula I+acifluorfen,compound of formula I+acifluorfen-sodium, compound of formulaI+aclonifen, compound of formula I+acrolein, compound of formulaI+alachlor, compound of formula I+alloxydim, compound of formula I+allylalcohol, compound of formula I+ametryn, compound of formulaI+amicarbazone, compound of formula I+amidosulfuron, compound of formulaI+aminopyralid, compound of formula I+amitrole, compound of formulaI+ammonium sulfamate, compound of formula I+anilofos, compound offormula I+asulam, compound of formula I+atraton, compound of formulaI+atrazine, compound of formula I+azimsulfuron, compound of formulaI+BCPC, compound of formula I+beflubutamid, compound of formulaI+benazolin, compound of formula I+benfluralin, compound of formulaI+benfuresate, compound of formula I+bensulfuron, compound of formulaI+bensulfuron-methyl, compound of formula I+bensulide, compound offormula I+bentazone, compound of formula I+benzfendizone, compound offormula I+benzobicyclon, compound of formula I+benzofenap, compound offormula I+bifenox, compound of formula I+bilanafos, compound of formulaI+bispyribac, compound of formula I+bispyribac-sodium, compound offormula I+borax, compound of formula I+bromacil, compound of formulaI+bromobutide, compound of formula I+bromoxynil, compound of formulaI+butachlor, compound of formula I+butafenacil, compound of formulaI+butamifos, compound of formula I+butralin, compound of formulaI+butroxydim, compound of formula I+butylate, compound of formulaI+cacodylic acid, compound of formula I+calcium chlorate, compound offormula I+cafenstrole, compound of formula I+carbetamide, compound offormula I+carfentrazone, compound of formula I+carfentrazone-ethyl,compound of formula I+CDEA, compound of formula I+CEPC; compound offormula I+chlorflurenol, compound of formula I+chlorflurenol-methyl,compound of formula I+chloridazon, compound of formula I+chlorimuron,compound of formula I+chlorimuron-ethyl, compound of formulaI+chloroacetic acid, compound of formula I+chlorotoluron, compound offormula I+chlorpropham, compound of formula I+chlorsulfuron, compound offormula I+chlorthal, compound of formula I+chlorthal-dimethyl, compoundof formula I+cinidon-ethyl, compound of formula I+cinmethylin, compoundof formula I+cinosulfuron, compound of formula I+cisanilide, compound offormula I+clethodim, compound of formula I+clodinafop, compound offormula I+clodinafop-propargyl, compound of formula I+clomazone,compound of formula I+clomeprop, compound of formula I+clopyralid,compound of formula I+cloransulam, compound of formulaI+cloransulam-methyl, compound of formula I+CMA, compound of formulaI+4-CPB, compound of formula I+CPMF, compound of formula I+4-CPP,compound of formula I+CPPC, compound of formula I+cresol, compound offormula I+cumyluron, compound of formula I+cyanamide, compound offormula I+cyanazine, compound of formula I+cycloate, compound of formulaI+cyclosulfamuron, compound of formula I+cycloxydim, compound of formulaI+cyhalofop, compound of formula I+cyhalofop-butyl, compound of formulaI+2,4-D, compound of formula I+3,4-DA, compound of formula I+daimuron,compound of formula I+dalapon, compound of formula I+dazomet, compoundof formula I+2,4-DB, compound of formula I+3,4-DB, compound of formulaI+2,4-DEB, compound of formula I+desmedipham, compound of formulaI+dicamba, compound of formula I+dichlobenil, compound of formulaI+ortho-dichlorobenzene, compound of formula I+para-dichlorobenzene,compound of formula I+dichlorprop, compound of formula I+dichlorprop-P,compound of formula I+diclofop, compound of formula I+diclofop-methyl,compound of formula I+diclosulam, compound of formula I+difenzoquat,compound of formula I+difenzoquat metilsulfate, compound of formulaI+diflufenican, compound of formula I+diflufenzopyr, compound of formulaI+dimefuron, compound of formula I+dimepiperate, compound of formulaI+dimethachlor, compound of formula I+dimethametryn, compound of formulaI+dimethenamid, compound of formula I+dimethenamid-P, compound offormula I+dimethipin, compound of formula I+dimethylarsinic acid,compound of formula I+dinitramine, compound of formula I+dinoterb,compound of formula I+diphenamid, compound of formula I+diquat, compoundof formula I+diquat dibromide, compound of formula I+dithiopyr, compoundof formula I+diuron, compound of formula I+DNOC, compound of formulaI+3,4-DP, compound of formula I+DSMA, compound of formula I+EBEP,compound of formula I+endothal, compound of formula I+EPTC, compound offormula I+esprocarb, compound of formula I+ethalfluralin, compound offormula I+ethametsulfuron, compound of formula I+ethametsulfuron-methyl,compound of formula I+ethofumesate, compound of formula I+ethoxyfen,compound of formula I+ethoxysulfuron, compound of formula I+etobenzanid,compound of formula I+fenoxaprop-P, compound of formulaI+fenoxaprop-P-ethyl, compound of formula I+fentrazamide, compound offormula I+ferrous sulfate, compound of formula I+flamprop-M, compound offormula I+flazasulfuron, compound of formula I+florasulam, compound offormula I+fluazifop, compound of formula I+fluazifop-butyl, compound offormula I+fluazifop-P, compound of formula I+fluazifop-P-butyl, compoundof formula I+flucarbazone, compound of formula I+flucarbazone-sodium,compound of formula I+flucetosulfuron, compound of formulaI+fluchloralin, compound of formula I+flufenacet, compound of formulaI+flufenpyr, compound of formula I+flufenpyr-ethyl, compound of formulaI+flumetsulam, compound of formula I+flumiclorac, compound of formulaI+flumiclorac-pentyl, compound of formula I+flumioxazin, compound offormula I+fluometuron, compound of formula I+fluoroglycofen, compound offormula I+fluoroglycofen-ethyl, compound of formula I+flupropanate,compound of formula I+flupyrsulfuron, compound of formulaI+flupyrsulfuron-methyl-sodium, compound of formula I+flurenol, compoundof formula I+fluridone, compound of formula I+fluorochloridone, compoundof formula I+fluoroxypyr, compound of formula I+flurtamone, compound offormula I+fluthiacet, compound of formula I+fluthiacet-methyl, compoundof formula I+fomesafen, compound of formula I+foramsulfuron, compound offormula I+fosamine, compound of formula I+glufosinate, compound offormula I+glufosinate-ammonium, compound of formula I+glyphosate,compound of formula I+halosulfuron, compound of formulaI+halosulfuron-methyl, compound of formula I+haloxyfop, compound offormula I+haloxyfop-P, compound of formula I+HC-252, compound of formulaI+hexazinone, compound of formula I+imazamethabenz, compound of formulaI+imazamethabenz-methyl, compound of formula I+imazamox, compound offormula I+imazapic, compound of formula I+imazapyr, compound of formulaI+imazaquin, compound of formula I+imazethapyr, compound of formulaI+imazosulfuron, compound of formula I+indanofan, compound of formulaI+iodomethane, compound of formula I+iodosulfuron, compound of formulaI+iodosulfuron-methyl-sodium, compound of formula I+ioxynil, compound offormula I+isoproturon, compound of formula I+isouron, compound offormula I+isoxaben, compound of formula I+isoxachlortole, compound offormula I+isoxaflutole, compound of formula I+karbutilate, compound offormula I+lactofen, compound of formula I+lenacil, compound of formulaI+linuron, compound of formula I+MAA, compound of formula I+MAMA,compound of formula I+MCPA, compound of formula I+MCPA-thioethyl,compound of formula I+MCPB, compound of formula I+mecoprop, compound offormula I+mecoprop-P, compound of formula I+mefenacet, compound offormula I+mefluidide, compound of formula I+mesosulfuron, compound offormula I+mesosulfuron-methyl, compound of formula I+mesotrione,compound of formula I+metam, compound of formula I+metamifop, compoundof formula I+metamitron, compound of formula I+metazachlor, compound offormula I+methabenzthiazuron, compound of formula I+methylarsonic acid,compound of formula I+methyldymron, compound of formula I+methylisothiocyanate, compound of formula I+metobenzuron, compound of formulaI+metolachlor, compound of formula I+S-metolachlor, compound of formulaI+metosulam, compound of formula I+metoxuron, compound of formulaI+metribuzin, compound of formula I+metsulfuron, compound of formulaI+metsulfuron-methyl, compound of formula I+MK-616, compound of formulaI+molinate, compound of formula I+monolinuron, compound of formulaI+MSMA, compound of formula I+naproanilide, compound of formulaI+napropamide, compound of formula I+naptalam, compound of formulaI+neburon, compound of formula I+nicosulfuron, compound of formulaI+nonanoic acid, compound of formula I+norflurazon, compound of formulaI+oleic acid (fatty acids), compound of formula I+orbencarb, compound offormula I+orthosulfamuron, compound of formula I+oryzalin, compound offormula I+oxadiargyl, compound of formula I+oxadiazon, compound offormula I+oxasulfuron, compound of formula I+oxaziclomefone, compound offormula I+oxyfluorfen, compound of formula I+paraquat, compound offormula I+paraquat dichloride, compound of formula I+pebulate, compoundof formula I+pendimethalin, compound of formula I+penoxsulam, compoundof formula I+pentachlorophenol, compound of formula I+pentanochlor,compound of formula I+pentoxazone, compound of formula I+pethoxamid,compound of formula I+petrolium oils, compound of formulaI+phenmedipham, compound of formula I+phenmedipham-ethyl, compound offormula I+picloram, compound of formula I+picolinafen, compound offormula I+pinoxaden, compound of formula I+piperophos, compound offormula I+potassium arsenite, compound of formula I+potassium azide,compound of formula I+pretilachlor, compound of formula I+primisulfuron,compound of formula I+primisulfuron-methyl, compound of formulaI+prodiamine, compound of formula I+profluazol, compound of formulaI+profoxydim, compound of formula I+prometon, compound of formulaI+prometryn, compound of formula I+propachlor, compound of formulaI+propanil, compound of formula I+propaquizafop, compound of formulaI+propazine, compound of formula I+propham, compound of formulaI+propisochlor, compound of formula I+propoxycarbazone, compound offormula I+propoxycarbazone-sodium, compound of formula I+propyzamide,compound of formula I+prosulfocarb, compound of formula I+prosulfuron,compound of formula I+pyraclonil, compound of formula I+pyraflufen,compound of formula I+pyraflufen-ethyl, compound of formulaI+pyrazolynate, compound of formula I+pyrazosulfuron, compound offormula I+pyrazosulfuron-ethyl, compound of formula I+pyrazoxyfen,compound of formula I+pyribenzoxim, compound of formula I+pyributicarb,compound of formula I+pyridafol, compound of formula I+pyridate,compound of formula I+pyriftalid, compound of formula I+pyriminobac,compound of formula I+pyriminobac-methyl, compound of formulaI+pyrimisulfan, compound of formula I+pyrithiobac, compound of formulaI+pyrithiobac-sodium, compound of formula I+quinclorac, compound offormula I+quinmerac, compound of formula I+quinoclamine, compound offormula I+quizalofop, compound of formula I+quizalofop-P, compound offormula I+rimsulfuron, compound of formula I+sethoxydim, compound offormula I+siduron, compound of formula I+simazine, compound of formulaI+simetryn, compound of formula I+SMA, compound of formula I+sodiumarsenite, compound of formula I+sodium azide, compound of formulaI+sodium chlorate, compound of formula I+sulcotrione, compound offormula I+sulfentrazone, compound of formula I+sulfometuron, compound offormula I+sulfometuron-methyl, compound of formula I+sulfosate, compoundof formula I+sulfosulfuron, compound of formula I+sulfuric acid,compound of formula I+tar oils, compound of formula I+2,3,6-TBA,compound of formula I+TCA, compound of formula I+TCA-sodium, compound offormula I+tebuthiuron, compound of formula I+tepraloxydim, compound offormula I+terbacil, compound of formula I+terbumeton, compound offormula I+terbuthylazine, compound of formula I+terbutryn, compound offormula I+thenylchlor, compound of formula I+thiazopyr, compound offormula I+thifensulfuron, compound of formula I+thifensulfuron-methyl,compound of formula I+thiobencarb, compound of formula I+tiocarbazil,compound of formula I+topramezone, compound of formula I+tralkoxydim,compound of formula I+tri-allate, compound of formula I+triasulfuron,compound of formula I+triaziflam, compound of formula I+tribenuron,compound of formula I+tribenuron-methyl, compound of formula I+tricamba,compound of formula I+triclopyr, compound of formula I+trietazine,compound of formula I+trifloxysulfuron, compound of formulaI+trifloxysulfuron-sodium, compound of formula I+trifluralin, compoundof formula I+triflusulfuron, compound of formulaI+triflusulfuron-methyl, compound of formula I+trihydroxytriazine,compound of formula I+tritosulfuron, compound of formulaI+[3-[2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]aceticacid ethyl ester (CAS RN 353292-31-6), compound of formulaI+4-[(4,5-dihydro-3-methoxy-4-methyl-5-oxo)-1H-1,2,4-triazol-1-ylcarbonylsulfamoyl]-5-methylthiophene-3-carboxylicacid (BAY636), compound of formula I+BAY747 (CAS RN 335104-84-2),compound of formula I+topramezone (CAS RN 210631-68-8), compound offormulaI+4-hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1]oct-3-en-2-one(CAS RN 352010-68-5), and compound of formulaI+4-hydroxy-3-[[2-(3-methoxypropyl)-6-(difluoromethyl)-3-pyridinyl]carbonyl]-bicyclo[3.2.1]oct-3-en-2-one.

The mixing partners for the compound of formula I may also be in theform of esters or salts, as mentioned e.g. in The Pesticide Manual, 12thEdition (BCPC) 2000.

The compounds of formula I according to the invention can also be usedin combination with safeners. Preferably, in these mixtures, thecompound of the formula I is one of those compounds listed in Tables 1to 146 below. The following mixtures with safeners, especially, comeinto consideration:

compound of formula I+cloquintocet-mexyl, compound of formulaI+cloquintocet acid and salts thereof, compound of formulaI+fenchlorazole-ethyl, compound of formula I+fenchlorazole acid andsalts thereof, compound of formula I+mefenpyr-diethyl, compound offormula I+mefenpyr diacid, compound of formula I+isoxadifen-ethyl,compound of formula I+isoxadifen acid, compound of formula I+furilazole,compound of formula I+furilazole R isomer, compound of formula(I)+N-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide,compound of formula I+benoxacor, compound of formula I+dichlormid,compound of formula I+AD-67, compound of formula I+oxabetrinil, compoundof formula I+cyometrinil, compound of formula I+cyometrinil Z-isomer,compound of formula I+fenclorim, compound of formula I+cyprosulfamide,compound of formula I+naphthalic anhydride, compound of formulaI+flurazole, compound of formula I+CL 304,415, compound of formulaI+dicyclonon, compound of formula I+fluxofenim, compound of formulaI+DKA-24, compound of formula I+R-29148 and compound of formulaI+PPG-1292. A safening effect can also be observed for the mixturescompound of the formula I+dymron, compound of the formula I+MCPA,compound of the formula I+mecopropand compound of the formulaI+mecoprop-P.

The above-mentioned safeners and herbicides are described, for example,in the Pesticide Manual, Twelfth Edition, British Crop ProtectionCouncil, 2000. R-29148 is described, for example by P. B. Goldsbrough etal., Plant Physiology, (2002), Vol. 130 pp. 1497-1505 and referencestherein, PPG-1292 is known from WO09211761 andN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide isknown from EP365484.

Benoxacor, cloquintocet-mexyl, cyprosulfamide, mefenpyr-diethyl andN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamideare especially preferred, where cloquintocet-mexyl is particularlyvaluable.

It is preferred to apply the other herbicide together with one of thesafeners mentioned above.

The following Examples illustrate the invention further but do not limitthe invention.

PREPARATION EXAMPLES

Those skilled in the art will appreciate that certain compoundsdescribed below are β-ketoenols, and as such may exist as a singletautomer or as a mixture of keto-enol and diketone tautomers, asdescribed, for example by J. March, Advanced Organic Chemistry, thirdedition, John Wiley and Sons. The compounds shown below, and in Table T1are drawn as an arbitrary single enol tautomer, but it should beinferred that this description covers both the diketone form and anypossible enols which could arise through tautomerism. Where more thanone tautomer is observed in proton NMR, the data shown are for themixture of tautomers. Furthermore, some of the compounds shown below aredrawn as single enantiomers for the purposes of simplicity, but unlessspecified as single enantiomers, these structures should be construed asrepresenting a mixture of enantiomers. Additionally, some of thecompounds can exist as diastereoisomers, and it should be inferred thatthese can be present as a mixture of diastereoisomers or as any possiblesingle diastereoisomer. Within the detailed experimental section thediketone tautomer is chosen for naming purposes, even if the predominanttautomer is the enol form.

Example 1 Preparation of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

Step 1: Preparation of(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-ene-3,5-dione

Furan (13.9 ml, 0.19 mol) is added to cyclopentene-1,4-dione (18.4 g,0.19 mol) and the reaction mixture is stirred at room temperature for 5days. The mixture is diluted with methanol and(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-ene-3,5-dione iscollected by filtration, and used without further purification in thenext step.

Step 2: Preparation of(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-ene-3,5-dione (2.1g, 12.8 mmol), prepared in Step 1, is dissolved in warm methanol (180ml) and the mixture is allowed to cool to room temperature. The mixtureis then hydrogenated in the presence of 5% palladium on carbon (approx.50 mg) at 3.5 bar for 4 hours. The catalyst is removed by filtrationthrough diatomaceous earth and the filtrate is concentrated underreduced pressure to afford(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

Step 3: Preparation of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

Iodobenzene diacetate (10.3 g, 32.0 mol) and sodium carbonate (3.38 g,32.0 mmol) are suspended in water (100 ml) and the resultant yellowsuspension is stirred at room temperature for 30 minutes. Meanwhile,(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione (5.3 g,32.0 mol) is added to a solution of sodium carbonate (3.38 g, 32.0 mol)in water (50 ml) and ethanol (50 ml) and the mixture is stirred at roomtemperature to produce an orange solution. The two mixtures are combinedand stirred for 3 hours at room temperature, then the mixture is pouredinto water and extracted with dichloromethane. The organic extracts arecombined, dried over anhydrous magnesium sulfate, filtered and thefiltrate evaporated under reduced pressure to give an iodonium ylide,used without further purification in the next step.

The iodonium ylide (3 g, 8.15 mmol), prepared above, is added to asolution of 2,6-diethyl-4-methylphenylboronic acid (1.57 g, 8.15 mmol),tetrabutylammonium bromide (2.63 g, 8.15 mmol), lithium hydroxidemonohydrate (1.03 g, 24.5 mmol) and palladium (II)acetate (92 mg, 0.41mmol) in 1,2-dimethoxyethane (80 ml) and water (20 ml) and the reactionmixture is heated at 50° C. for 5 hours under an atmosphere of nitrogen.The reaction mixture is cooled to room temperature and partitionedbetween dilute aqueous hydrochloric acid and ethyl acetate. The organicphase is then extracted into 0.5 M aqueous potassium carbonate solutionand the organic phase discarded. The aqueous phase is acidified withconcentrated hydrochloric acid and extracted with ethyl acetate. Theorganic extract is dried over anhydrous magnesium sulfate, filtered andthe filtrate concentrated under reduced pressure. The residue ispurified by column chromatography on silica gel to afford(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.88-6.87 (2H, m), 4.55-4.54 (2H, m), 2.62(2H, s), 2.36-2.27 (7H, m), 1.69-1.67 (2H, m), 1.40-1.39 (2H, m), 1.03(6H, q).

Example 2 Preparation of (1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one

Step 1: Preparation of 2-bromo-3-methoxycyclopent-2-enone

N-Bromosuccinimide (24.92 g, 0.140 mol) is added, portionwise, over 1hour to a stirred solution of 3-methoxycyclopent-2-enone (14.95 g, 0.133mol) in 1,2-dichloroethane (300 ml) at 0° C. in an amber flask. Thereaction mixture is stirred at 0° C. for a further 90 minutes and thenany remaining solid is removed by filtration. The filtrate is evaporatedto dryness under reduced pressure, the resultant solid is dissolved inwarm toluene (600 ml) and washed quickly with ice-cold water (2×100 ml).The organic phase is dried over anhydrous magnesium sulfate, filteredand the filtrate evaporated under reduced pressure until approximately150 ml remains. The residue is cooled with an ice bath and left for 30minutes. The resultant solid is removed by filtration, washed withhexane (50 ml) and air-dried to give 2-bromo-3-methoxycyclopent-2-enone.

Step 2: Preparation of2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

To a stirred suspension of 2-bromo-3-methoxycyclopent-2-enone (17.5 g,91.6 mmol), 2,6-diethyl-4-methylphenyl boronic acid (26.4 g, 137 mmol)and freshly powdered potassium phosphate (38.9 g, 183 mmol) inanhydrous, degassed toluene (450 ml) under a nitrogen atmosphere areadded palladium (II)acetate (0.411 g, 1.83 mmol) and2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (1.51 g, 3.67 mmol). Thereaction mixture is heated at 90° C. for 6.5 hours and then allowed tocool to room temperature overnight. The reaction is diluted with water(400 ml) and extracted with ethyl acetate (3×150 ml). The combinedorganic extracts are washed with brine (50 ml), dried over anhydrousmagnesium sulfate, filtered and the filtrate is evaporated to drynessunder reduced pressure to give a brown oil. The crude product ispurified by column chromatography on silica gel to give2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

Step 3: Preparation of5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone

To a stirred solution of2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone (0.715 g, 2.77mmol) in 1,4-dioxane (45 ml), and under an atmosphere of nitrogen, areadded copper (II) chloride (0.743 g, 5.53 mmol) and lithium chloride(0.176 g, 4.15 mmol). The reaction is heated at reflux for 7 hours andallowed to cool to room temperature overnight. The remaining solid isremoved by filtration and washed with ethyl acetate (50 ml). Thefiltrate is washed with water (2×25 ml) and the aqueous washingsre-extracted with ethyl acetate (1.5 ml). The combined organic phasesare washed with brine (15 ml), dried over anhydrous magnesium sulfate,filtered and the filtrate is evaporated under reduced pressure to give abrown oil. The crude product is purified by column chromatography onsilica gel to give5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone.

Step 4: Preparation of(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one

To a stirred solution of5-chloro-2-(2,6-diethyl-4-methylphenyl)-3-methoxycyclopent-2-enone(0.530 g, 1.81 mmol) in furan (40 ml) at room temperature is added bysyringe pump over two hours a solution of1,8-diazabicyclo[5.4.0]undec-7-ene (0.540 ml, 3.62 mmol) in furan (10ml). The reaction is stirred at room temperature for a further 30minutes and then evaporated to dryness under reduced pressure. Theresidue is diluted with water (50 ml), 2 M aqueous hydrochloric acid (25ml) is added and the mixture is extracted with ethyl acetate (3×50 ml).The combined organic extracts are washed with brine (20 ml), dried overanhydrous magnesium sulfate, filtered and the filtrate is evaporated todryness under reduced pressure. The residue is purified by columnchromatography on silica gel to give(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.90 (2H, s), 6.45 (1H, dd), 6.35 (1H,dd), 5.30 (1H, d), 5.25 (1H, d), 3.65 (3H, s), 3.65 (1H, dd), 3.45 (1H,dd), 2.35 (4H, m), 2.30 (3H, s), 1.10 (6H, m).

Note: A quantity of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-oneis also formed during the course of this reaction.

Example 3 Preparation of(1RS,2RS,6SS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]dec-4-en-3-one

To a solution of(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one(0.052 g, 0.16 mmol) in methanol (10 ml) is added 5% palladium on carbon(10 mg). The reaction is stirred under an atmosphere of hydrogen for 90minutes. The reaction is filtered through diatomaceous earth and thefilter pad is washed with ethyl acetate (10 ml). The solvent is removedunder reduced pressure to yield(1RS,2RS,6-SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]dec-4-en-3-one.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.90 (2H, m), 4.85 (2H, m), 3.70 (3H, s),3.60 (1H, m), 3.35 (1H, dd), 2.50 (2H, m), 2.35 (2H, m), 2.30 (3H, s),1.90-1.75 (4H, m), 1.20 (3H, t), 1.10 (3H, t).

Example 4 Preparation of(1RS,2RS,6SS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

To a solution of(1RS,2RS,6SR,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxa-tricyclo[5.2.1.0^(2,6)]dec-4-en-3-one(0.049 g, 0.15 mmol) in THF (1 ml) in a 5 ml microwave vial is added 2 Maqueous hydrochloric acid (4 ml). The reaction mixture is at 140° C.under microwave irradiation for 50 minutes. The reaction mixture iscooled to room temperature, diluted with 2 M aqueous potassium carbonatesolution (20 ml) and washed with diethyl ether (2×5 ml). The pH of theaqueous phase is adjusted to approx. 2 by addition of 5 M aqueoushydrochloric acid and then extracted with ethyl acetate (3×10 ml). Thecombined organic extracts are washed with brine (10 ml), dried overanhydrous magnesium sulfate, filtered and the filtrate is evaporated todryness under reduced pressure to give a yellow oil. The crude productis purified by column chromatography on silica gel to give(1RS,2RS,6SS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.95 (2H, s), 4.75 (2H, br), 3.40 (2H,br), 2.45 (2H, q), 2.35 (2H, q), 2.30 (3H, s), 1.80 (4H, m), 1.15 (3H,t), 1.05 (3H, t).

Example 5 Preparation of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one

Step 1: Preparation of(1RS,2SR,6RS,7SR)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one

Iodine (0.10 g, 0.38 mmol) is added to a solution of(1RS,2SR,6RS,7SR)-10-oxa-tricyclo[5.2.1.0^(2,6)]decane-3,5-dione (2.1 g,12.65 mmol) in methanol (50 ml) and the reaction mixture is stirred for2 hours at room temperature. The solvent is then removed under reducedpressure, dichloromethane is added and the organic layer is washed withsaturated aqueous sodium thiosulfate solution, water and brine. Theorganic layer is dried over anhydrous magnesium sulfate, filtered andthe filtrate is evaporated under reduced pressure to give(1RS,2SR,6RS,7SR)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-oneand used without further purification in the next step.

Step 2: Preparation of(1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one

A solution of bromine (0.14 ml, 2.8 mmol) in dichloromethane (5 ml) isadded dropwise to a solution of the enol ether (0.48 g, 2.6 mmol)prepared in step 1 in dichloromethane (40 ml) at 0° C. and the reactionmixture is stirred for 1 hour. Triethylamine (0.64 ml, 4.6 mmol) is thenadded and the reaction mixture is allowed to warm to room temperatureand then stirred for 3 hours. The reaction mixture is washed with 2Maqueous hydrochloric acid and brine, dried over anhydrous magnesiumsulfate, filtered and the filtrate evaporated under reduced pressure.The residue is purified by column chromatography on silica gel to give(1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one.

Step 3: Preparation of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one

A mixture of (1RS,2SR,6RS,7SR)-4-bromo-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one(0.315 g, 1.2 mmol), 2,6-diethyl-4-methylphenylboronic acid (0.35 g, 1.8mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (20 mg, 0.048mmol), palladium (II)acetate (5.5 mg, 0.024 mmol) and potassiumphosphate (0.51 g, 2.4 mmol) are heated in degassed toluene at 95° C.for 24 hours. The reaction mixture is partitioned betweendichloromethane and water, and the organic phase is dried over anhydrousmagnesium sulfate, filtered and the filtrate is evaporated under reducedpressure. The residue is purified by column chromatography on silica gelto give(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-5-methoxy-10-oxatricyclo[5.2.1.0^(2,6)]dec-4-en-3-one.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.90 (1H, s), 6.80 (1H, s), 4.73 (1H, d),4.66 (1H, d), 3.58 (3H, s), 2.91 (1H, d), 2.66 (1H, d), 2.50-2.36 (4H,m), 2.30 (3H, s), 1.88-1.81 (2H, m), 1.62-1.56 (2H, m), 1.12-1.09 (6H,m).

Example 6 Preparation of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione

Step 1: Preparation of (2,4,6-trimethylphenyl)furan-2-ylmethanol

A solution of 2,4,6-trimethyl-1-bromobenzene (30.9 g, 155 mmol) intetrahydrofuran (100 ml) is added slowly to magnesium turnings (3.77 g,155 mmol), until the magnesium is just covered. A small quantity ofiodine is added and the mixture is allowed to stand at room temperaturefor 25 minutes and then heated and stirred until the brown colour islost. The remainder of the aryl bromide solution is added dropwise overa 20 minute period, with occasional heating to maintain the formation ofthe Grignard reagent solution. The reaction is stirred at roomtemperature for 1 hour. A solution of furfural (12.8 ml, 155 mmol) intetrahydrofuran (70 ml) is added dropwise, and once the addition iscomplete, the reaction is stirred at room temperature for 2 hours. Thereaction is quenched by cautious addition of excess saturated ammoniumchloride solution, then extracted into ethyl acetate, washed with brine,dried over anhydrous magnesium sulfate, filtered and concentrated underreduced pressure. Purification by column chromatography on silica gelaffords (2,4,6-trimethylphenyl)furan-2-ylmethanol.

Step 2: Preparation of5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone

A solution of (2,4,6-trimethylphenyl)furan-2-ylmethanol (27.8 g, 129mmol) in acetone (730 ml) and water (100 ml) is heated to 55° C. andpolyphosphoric acid (2 g) is added. The mixture is stirred at 55° C. for7 hours, then cooled to room temperature overnight. The reaction mixtureis concentrated under reduced pressure to remove most of the acetonethen ethyl acetate (500 ml) is added, and the reaction mixture ispartitioned. The aqueous phase is extracted into ethyl acetate and theorganic solutions are combined, washed with saturated aqueous sodiumbicarbonate solution and brine, dried over anhydrous magnesium sulfate,filtered and the filtrate is concentrated under reduced pressure. Theresidue is purified by column chromatography on silica gel to give5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone.

Step 3: Preparation of2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione

Jones' reagent (138 ml of 1.67 M solution, 230 mmol) is added dropwiseover 40 minutes to a cooled (ice-bath) solution of5-(2,4,6-trimethylphenyl)-4-hydroxycyclopent-2-enone (49.66 g, 230 mmol)in acetone (600 ml). The mixture is stirred for 1 hour. Isopropanol (100ml) is added and the mixture is stirred at room temperature for 2 hours.The mixture is diluted with ethyl acetate and washed with brine, driedover anhydrous magnesium sulfate, filtered and the filtrate isevaporated under reduced pressure to give2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione.

Step 4: Preparation of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-en-3,5-dione

Furan (214 ml, 3.15 mol) and magnesium iodide (7.0 g, 0.025 mol) areadded to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (27.0 g,0.126 mol) and the mixture is stirred at room temperature for 4 days.The reaction mixture is concentrated under reduced pressure and theresidue is purified by column chromatography on silica gel to give(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.86 (2H, s), 6.47 (2H, s), 5.01 (2H, s),2.74 (2H, s), 2.23 (3H, s), 2.08 (3H, s), 2.06 (3H, s).

Example 7 Preparation of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A solution of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione(205 mg, 0.66 mmol) in methanol (250 ml) is hydrogenated at 2 bar over5% palladium on carbon (approximately 20 mgs) for 1 hour at roomtemperature. The catalyst is removed by filtration through diatomaceousearth and the solvent is evaporated under reduced pressure. Triturationwith diethyl ether gives(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, d₄-MeOH) δ_(H) 6.88 (2H, s), 4.61 (2H, s), 2.87 (2H,s), 2.27 (3H, s), 2.06 (6H, s), 1.84-1.82 (2H, m), 1.71-1.66 (2H, m).

Example 8 Preparation of(1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

3-(Trimethylsilylethynyl)furan (10.0 g, 61 mmol) and magnesium iodide(1.11 g, 4 mmol) are added to2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (4.34 g, 20 mmol) andthe mixture is stirred at room temperature for 3 days. The reactionmixture is concentrated under reduced pressure and the residue ispurified by column chromatography on silica gel to give(1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.65 (2H, s), 6.26 (1H, s), 4.75 (1H, s),4.67 (1H, s), 2.62 (1H, d), 2.52 (1H, d), 2.03 (3H, s), 1.84 (3H, s),1.80 (3H, s), 0.00 (9H, s).

Example 9 Preparation of(1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

Potassium carbonate (2.58 g, 19 mmol) is added to a stirred solution of(1RS,2SR,6RS,7RS)-4-(2,4,6-trimethylphenyl)-8-trimethylsilylethynyl-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione(6.43 g, 17 mmol) in methanol (100 ml). The reaction mixture is stirredat room temperature for 2 hours and 30 minutes, then dilute aqueoushydrochloric acid is added and the mixture is extracted with ethylacetate. The organic extracts are combined, dried over anhydrousmagnesium sulfate, filtered and the filtrate is evaporated under reducedpressure to give(1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, d₄-MeOH) δ_(H) 6.85 (2H, s), 6.72 (1H, d), 5.03 (1H,d), 3.96 (1H, s), 2.92-2.88 (2H, m), 2.24 (3H, s), 2.06 (3H, s), 2.01(3H, s).

Example 10 Preparation of(1RS,2SR,6RS,7SR,8RS)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dioneand(1RS,2SR,6RS,7SR,8SR)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A solution of(1RS,2SR,6RS,7RS)-8-ethynyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione(1.0 g, 3.3 mmol) in methanol (100 ml) and dichloromethane (100 ml) ishydrogenated at 3.5 bar over 5% palladium on carbon (approximately 50mg) until the reaction is judged to be complete by mass spectrometry.The catalyst is removed by filtration through diatomaceous earth and thesolvent is evaporated under reduced pressure. Purification by columnchromatography on silica gel gives an approximately 1:1 mixture of(1RS,2SR,6RS,7SR,8RS)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dioneand(1RS,2SR,6RS,7SR,8SR)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

(1RS,2SR,6RS,7SR,8RS)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione:¹H NMR (400 MHz, CDCl₃) δ_(H) 6.82 (2H, s), 4.44 (1H, d), 4.24 (1H, s),2.45-2.40 (2H, m), 2.22 (3H, s), 2.02 (6H, s), 1.58-1.52 (2H, m),1.38-1.33 (1H, m), 1.25-1.16 (2H, m), 0.85-0.82 (3H, m).

(1RS,2SR,6RS,7SR,8SR)-8-ethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione:¹H NMR (400 MHz, CDCl₃) δ_(H) 6.85 (2H, s), 4.51 (1H, d), 4.43 (1H, d),3.07 (1H, d), 2.82-2.81 (1H, m), 2.24 (3H, s), 2.10-2.05 (2H, m), 2.04(6H, s), 1.87-1.79 (1H, m), 1.53-1.46 (2H, m), 1.00 (3H, t).

Example 11 Preparation of(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione

Step 1: Preparation of (5-bromo-2-ethylphenyl)furan-2-ylmethanol

4-Bromo-2-iodoethyl benzene (50.0 g, 0.161 mol) is dissolved inanhydrous tetrahydrofuran (250 ml) and cooled to −70° C. under anatmosphere of nitrogen. Isopropylmagnesium chloride (2 M solution inTHF, 100 ml, 0.200 mmol) is added dropwise with vigorous stirring over40 minutes, maintaining the internal temp below −60° C. by externalcooling. When the addition is complete, the reaction is stirred at −70°C. for 20 minutes then allowed to warm to room temperature over 1 hourand 20 minutes. The reaction mixture is then cooled to −70° C. and asolution of 2-furaldehyde (16 ml, 18.6 g, 190 mmol) in tetrahydrofuran(50 ml) is added dropwise over 40 minutes. On completion of theaddition, the reaction is allowed to warm to room temperature andstirred at room temperature for 3 hours. Saturated aqueous ammoniumchloride solution (˜500 ml) is added and the mixture is extracted intoethyl acetate. The organic solutions are combined, washed with brine,dried over anhydrous magnesium sulfate and concentrated under reducedpressure. The residue is further purified by column chromatography onsilica gel to give (5-bromo-2-ethylphenyl)-furan-2-ylmethanol.

Step 2: Preparation of5-(5-bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone

A solution of (5-bromo-2-ethylphenyl)furan-2-ylmethanol (40.73 g, 0.145mol) in acetone (1150 ml) and water (170 ml) is heated to 55° C. and 30drops of polyphosphoric acid are added. The mixture is stirred at 55° C.for 44 hours, then cooled to room temperature. The reaction mixture isconcentrated under reduced pressure to remove most of the acetone thenethyl acetate (500 ml) is added, and the reaction mixture ispartitioned. The aqueous phase is extracted into ethyl acetate and theorganic solutions are combined, washed with saturated aqueous sodiumbicarbonate solution and brine, dried over anhydrous magnesium sulfate,filtered and the filtrate is concentrated under reduced pressure. Theresidue is purified by column chromatography on silica gel to give5-(5-bromo-2-ethylphenyl)-4-hydroxycyclopent-2-enone.

Step 3: Preparation of2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione

Jones' reagent (75 ml of 1.67 M solution, 125 mmol) is added dropwiseover 30 minutes to a cooled (ice-bath) solution of5-(5-bromo-4-ethylphenyl)-4-hydroxycyclopent-2-enone (33 g, 117 mmol) inacetone (400 ml). The mixture is stirred for 20 minutes, then thecooling bath is removed and the mixture is stirred for 1 hour at roomtemperature. Isopropanol (150 ml) is added to the yellow slurry and themixture is stirred at room temperature for 2 hours. The mixture isdiluted with ethyl acetate and washed with brine, dried over anhydrousmagnesium sulfate, filtered and the filtrate is evaporated under reducedpressure to give 2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione.

Step 4: Preparation of(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione

2,5-Dimethylfuran (2.3 ml, 21.6 mmol) and magnesium iodide (0.40 g, 1.4mmol) are added to a solution of2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (2.0 g, 7.2 mmol) indichloromethane (10 ml) and the mixture is stirred at room temperaturefor 3 days. The reaction mixture is concentrated under reduced pressureand the residue is purified by column chromatography on silica gel togive(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione.

¹H NMR (400 MHz, d₄-MeOH) δ_(H) 7.39 (1H, dd), 7.18 (1H, d), 7.16 (1H,d), 6.35 (2H, s), 2.79 (2H, s), 2.46 (2H, q), 1.61 (6H, s), 1.07 (3H,t).

Example 12 Preparation of(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A solution of(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione(1.63 g, 4.3 mmol) in methanol (200 ml) is hydrogenated at 3.5 bar over5% palladium on carbon for 1 hour and 30 minutes at room temperature.The catalyst is removed by filtration through diatomaceous earth and thesolvent is evaporated under reduced pressure. Trituration with diethylether gives(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-1,7-dimethyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, d₄-MeOH) δ_(H) 7.36 (1H, dd), 7.17 (1H, d), 7.15 (1H,d), 2.81 (2H, s), 2.48-2.43 (2H, m), 1.84-1.79 (2H, m), 1.69-1.65 (2H,m), 1.51 (6H, s), 1.08 (3H, t).

Example 13 Preparation of(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione

Furan (4.0 ml, 55.0 mmol) and magnesium iodide (1.00 g, 3.6 mmol) areadded to a solution of2-(5-bromo-2-ethylphenyl)cyclopent-4-ene-1,3-dione (5.0 g, 17.9 mmol) indichloromethane (20 ml) and the mixture is stirred at room temperaturefor 3 days. A further quantity of furan (1.3 ml, 17.8 mmol) is added andstirring continued for 18 hours, and then a further quantity of furan(1.3 ml, 17.8 mmol) is added and the mixture is stirred for 48 hours,and then allowed to stand at room temperature for 5 days. The reactionmixture is dissolved in methanol and concentrated under reducedpressure. The residue is purified by column chromatography on silica gelto give(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione.

¹H NMR (400 MHz, d₄-MeOH) δ_(H) 7.37 (1H, dd), 7.17 (1H, d), 7.14 (1H,d), 6.54 (2H, s), 4.96 (2H, s), 2.79 (2H, s), 2.44 (2H, q), 1.06 (3H, t)

Example 14 Preparation of (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A solution of (1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]-dec-8-en-3,5-dione(3.00 g, 8.6 mmol) in methanol (250 ml) is hydrogenated at 3.5 bar over5% palladium on carbon for 2 hours at room temperature. The catalyst isremoved by filtration through diatomaceous earth and the solvent isevaporated under reduced pressure to give(1RS,2SR,6RS,7SR)-4-(5-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, d_(a)-MeOH) δ_(H) 7.34 (1H, dd), 7.15 (2H, d), 4.59(2H, s), 2.78 (2H, s), 2.43 (2H, q), 1.81-1.78 (2H, m), 1.66-1.61 (2H,m), 1.06 (3H, t).

Example 15 Preparation of(1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-en-3,5-dione

3-Bromofuran (5.2 g, 56 mmol) and magnesium iodide (1.5 g, 5.6 mmol) areadded to 2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (4.0 g, 18.7mmol) and the mixture is stirred at room temperature for 2 days; smallquantities of dichloromethane are added when required to aid stirring.The reaction mixture is allowed to stand at room temperature for 17hours, then concentrated under reduced pressure. The residue is purifiedby column chromatography on silica gel to give (1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-en-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.87 (2H, s), 6.40 (1H, d), 4.95 (1H, s),4.82 (1H, s), 2.90 (1H, d), 2.81 (1H, d), 2.25 (3H, s), 2.07 (3H, s),2.03 (3H, s).

Example 16 Preparation of(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione

A mixture of(1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-en-3,5-dione(300 mg, 0.82 mmol), 4-fluorophenylboronic acid (171 mg, 1.22 mmol),sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl-3-sulfonatehydrate (17 mg, 0.03 mmol), potassium phosphate (522 mg, 2.5 mmol) andpalladium acetate (4 mg, 0.02 mmol) in water (8 ml) are heated for 150°C. for 25 minutes under microwave irradiation. The mixture is cooled toroom temperature and dilute aqueous hydrochloric acid is added. Themixture is filtered and the filtrate is extracted with ethyl acetate.The organic extracts are combined, dried over anhydrous magnesiumsulfate, filtered and the filtrate is concentrated under reducedpressure. Purification by column chromatography on silica gel gives(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 7.35-7.32 (2H, m), 6.86 (1H, s), 6.85 (1H,s), 6.82-6.77 (2H, m), 6.37 (1H, d), 5.31 (1H, s), 5.03 (1H, d),2.82-2.78 (2H, m), 2.25 (3H, s), 2.07 (3H, s), 2.05 (3H, s).

Example 17 Preparation of(1RS,2SR,6RS,7SR,8SR)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A suspension of(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione(99 mg, 0.26 mmol) in methanol (20 ml) is hydrogenated at 3 bar over 5%palladium on carbon for 5 hours at room temperature. The catalyst isremoved by filtration through diatomaceous earth and the solvent isevaporated under reduced pressure to give(1RS,2SR,6RS,7SR,8SR)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2g)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 7.39 (2H, dd), 7.11 (2H, t), 6.86 (1H, s),6.85 (1H, s), 4.73 (1H, d), 4.68 (1H, d), 3.63-3.58 (1H, m), 2.94 (1H,d), 2.75 (1H, d), 2.38-2.30 (1H, m), 2.25 (3H, s), 2.08 (3H, s), 2.03(3H, s), 1.92 (1H, dd).

Example 18 Preparation of(1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

Bis(triphenylphosphine)palladium diacetate (20 mg, 0.024 mmol),1-fluoro-3-iodo-benzene (104 mg, 0.47 mmol) and piperidine (0.16 ml, 1.6mmol) are added to a solution of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione(0.20 g, 0.71 mmol) in dry N,N-dimethylformamide (2 ml). Formic acid(0.06 ml, 1.6 mmol) is added and the reaction mixture is heated at 50°C. for 2 hours. The reaction mixture is cooled to room temperature,water (1 ml) and dichloromethane (1 ml) are added, and the mixture isstirred for 1 hour. The two phases are separated, the organic phasecollected and the solvent is evaporated. The residue is purified bypreparative reverse-phase HPLC to give(1RS,2SR,6RS,7SR,8RS)-8-(3-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 7.75-7.66 (1H, m), 7.25-7.21 (1H, m),7.06-7.02 (2H, m), 6.88 (1H, s), 6.87 (1H, s), 4.83 (1H, br. s), 4.59(1H, s), 3.00-2.98 (1H, m), 2.83-2.70 (2H, br. s), 2.25 (3H, s),2.20-2.16 (1H, m), 2.09 (3H, s), 2.08 (3H, s), 1.92-1.89 (1H, m).

Example 19 Preparation of(1RS,2SR,6RS,7SR,8RS)-8-[2,6-bis(trifluoromethyl)pyridin-4-yl]-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A mixture of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-en-3,5-dione(400 mg, 1.4 mmol), 2,6-bis(trifluoromethyl)-4-chloropyridine (531 mg,1.4 mmol), palladium acetate (16 mg, 0.07 mmol),2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl (67 mg, 0.14 mmol),potassium formate (353 mg, 4.2 mmol), tetrabutylammonium chloride (389mg, 1.4 mmol) and copper iodide (53 mg, 0.28 mmol) in dryN,N-dimethylformamide (6 ml) are heated, at 150° C. for 30 minutes undermicrowave irradiation. Purification by preparative reverse-phase HPLCgives(1RS,2SR,6RS,7SR,8RS)-8-[2,6-bis(trifluoromethyl)pyridin-4-yl]-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz d₄-MeOH) δ_(H) 7.81 (1H, s), 7.26 (1H, s), 6.92 (1H, s),6.90 (1H, s), 4.91 (1H, d), 4.64 (1H, s), 3.19-3.17 (1H, m), 2.99-2.95(2H, m), 2.32-2.27 (1H, m), 2.26 (3H, s), 2.09 (3H, s), 2.07 (3H, s),1.93-1.90 (1H, m).

Example 20 Preparation of (1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione

A mixture of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-3,5-dione(510 mg, 1.8 mmol), vinyl iodide (280 mg, 1.8 mmol), palladium acetate(20 mg, 0.09 mmol), sodium formate (454 mg, 5.4 mmol) andtetrabuylammonium chloride (500 mg, 1.8 mmol) in dryN,N-dimethylformamide (15 ml) are heated at 150° C. for 20 minutes undermicrowave irradiation. The mixture is cooled to room temperature andpartitioned between water and ethyl acetate. The organic extracts arecombined, dried over anhydrous magnesium sulfate, filtered and thefiltrate is evaporated under reduced pressure. The residue is purifiedby column chromatography on silica gel to give(1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.90-6.89 (2H, m), 5.80-5.71 (1H, m),5.05-4.97 (2H, m), 4.68 (1H, d), 4.44 (1H, s), 2.81-2.76 (2H, m),2.51-2.46 (1H, m), 2.26 (3H, s), 2.07 (3H, s), 2.06 (3H, s), 1.89-1.84(1H, m), 1.67-1.62 (1H, m).

Example 21 Preparation of methyl [(1RS,2SR,6RS,7SR.8RS)-3,5-dioxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-yl]acrylate

Benzylidene[1,3-bis(2,4,6-trimethylphenyl)-2-imidazolidinylidene]dichloro(tricyclohexyl-phosphine)ruthenium(14 mg, 0.016 mmol) is added to a suspension of(1RS,2SR,6RS,7SR,8RS)-4-(2,4,6-trimethylphenyl)-8-vinyl-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione(100 mg, 0.32 mmol) and methyl acrylate (0.03 ml, 0.35 mmol) indichloromethane (1 ml) and the mixture is stirred at reflux for 2 hours.The reaction mixture is cooled to room temperature, the solventevaporated under reduced pressure and the residue is purified by columnchromatography on silica gel to give methyl[1RS,2SR,6RS,7SR,8RS)-3,5-dioxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-yl]acrylate.Proton NMR indicates the product comprises a mixture of E- andZ-isomers.

E-Isomer: ¹H NMR (400 MHz, CDCl₃) δ_(H) 6.80 (2H, s), 6.74 (1H, dd),5.91 (1H, d), 4.58 (1H, d), 4.30 (1H, s), 3.33 (3H, s), 2.85-2.77 (3H,m), 2.21 (3H, s), 1.97 (3H, s), 194 (3H, s), 1.94-1.91 (1H, m),1.59-1.54 (1H, m).

Example 22 Preparation of(1RS,2SR,6SR,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-ene-3,5-dione

Furfuryl alcohol (4 ml, 46.7 mmol) is added to2-(2,4,6-trimethylphenyl)cyclopent-4-ene-1,3-dione (2.0 g, 9.3 mmol) andMgI₂ (520 mg, 1.86 mmol) and the reaction is stirred for 17 hours. Thereaction mixture is adsorbed onto silica gel and purified by columnchromatography on silica gel to give(1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-ene-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.87 (2H, s), 6.49 (1H, d), 6.44 (1H, d),4.96 (1H, d), 3.98 (1H, d), 3.85 (1H, d), 2.82-2.78 (2H, m), 2.24 (3H,s), 2.08 (3H, s), 2.05 (3H, s).

Example 23 Preparation of tert-butyl carbamic acid[(1RS,2SR,6RS,7SR)-3,5-dioxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-1-yl]methylester

Step 1: Preparation of(1RS,2SR,6SR,7SR)-5-benzyloxy-7-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-oneand(1RS,2SR,6RS,7SR)-5-benzyloxy-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one

Benzyl bromide (0.72 ml, 6.1 mmol) is added to a mixture of potassiumcarbonate (840 mg, 6.1 mmol) and(1RS,2SR,6RS,7SR)-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]dec-8-ene-3,5-dione(1.80 g, 5.8 mmol) in acetone (80 ml), and the reaction mixture isheated at reflux for 4 hours. The reaction mixture is cooled to roomtemperature, diluted with water and extracted with ethyl acetate. Theorganic extracts are combined, dried over anhydrous magnesium sulfate,filtered and the filtrate is concentrated under reduced pressure. Theresidue is purified by column chromatography on silica gel to give amixture of(1RS,2SR,6SR,7SR)-5-benzyloxy-7-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-oneand(1RS,2SR,6RS,7SR)-5-benzyloxy-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one.

Step 2: Preparation of tert-butyl carbamic acid[(1RS,2RS,6RS,7SR)-3-benzyloxy-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester and tert-butyl carbamic acid[(1RS,2SR,6RS,7SR)-5-benzyloxy-3-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester

Sodium hydride (60 mg, 1.97 mmol) is added to a cooled (0° C.) mixtureof(1RS,2SR,6SR,7SR)-5-benzyloxy-7-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-oneand(1RS,2SR,6RS,7SR)-5-benzyloxy-1-hydroxymethyl-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]deca-4,8-dien-3-one(265 mg, 0.66 mmol) in tetrahydrofuran (10 ml). The mixture is stirredfor a few minutes and then tert-butyl isocyanate (0.15 ml, 1.32 mmol) isadded. The reaction is allowed warm to room temperature and stirred for17 hours. The mixture is partitioned between water and ethyl acetate,and the organic solutions are combined, dried over anhydrous magnesiumsulfate, filtered and the filtrate is evaporated. The residue ispurified by column chromatography on silica gel to give a mixture oftert-butyl carbamic acid[(1RS,2RS,6RS,7SR)-3-benzyloxy-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester and tert-butyl carbamic acid[(1RS,2SR,6RS,7SR)-5-benzyloxy-3-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester.

Step 3: Preparation of tert-butyl carbamic acid[(1RS,2SR,6RS,7SR)-3,5-dioxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-1-yl]methylester

A suspension of a mixture of[(1RS,2RS,6RS,7SR)-3-benzyloxy-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester and tert-butyl carbamic acid [(1RS,2SR,6RS,7SR)-5-benzyloxy-3-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]deca-4,8-dien-1-yl]methylester (147 mg, 0.29 mmol) in methanol (20 ml) is hydrogenated at 3 barover 5% palladium on carbon for 5 hours. The catalyst is removed byfiltration and the filtrate is concentrated under reduced pressure togive tert-butyl carbamic acid[(1RS,2SR,6RS,7SR)-3,5-dioxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-8-en-1-yl]methyl.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.83 (2H, s), 5.02 (1H, s), 4.72 (1H, d),4.65 (1H, d), 4.12 (1H, d), 2.83 (1H, d), 2.70 (1H, d), 2.23 (3H, s),2.07 (3H, s), 2.06 (3H, s), 1.86-1.80 (2H, m), 1.57-1.45 (2H, m), 1.29(9H, s).

Example 24 Preparation of(1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

Step 1: Preparation of 4-bromo-2-ethylphenyllead triacetate

Dry chloroform (30 ml) is added to a mixture of lead tetraacetate (8.52g, 19.3 mmol) and mercuric diacetate (0.28 g, 0.875 mmol) under anatmosphere of nitrogen, and the reaction mixture is stirred and heatedto 40° C. 4-Bromo-2-ethylphenylboronic acid (4.0 g, 17.5 mmol) is addedin one portion and the mixture is stirred at 40° C. for 4 hours. Thereaction mixture is cooled to 0° C., and potassium carbonate (2.66 g,19.3 mmol) is added portionwise. The mixture is stirred for 5 minutes,then filtered through a small plug of diatomaceous earth, washing withchloroform. The filtrate concentrated under reduced pressure to give4-bromo-2-ethylphenyllead triacetate.

Step 2: Preparation of(1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione

4-Dimethylaminopyridine (3.67 g, 30.0 mmol) and toluene (10 ml) areadded to a solution of(1RS,2SR,6RS,7SR)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione (1.0 g,6.0 mmol) in chloroform (40 ml) and the reaction mixture is heated to80° C. 4-Bromo-2-ethylphenyllead triacetate (5.13 g, 9.04 mmol) is addedportionwise over 20 minutes, and once the addition is complete thereaction mixture is stirred at 80° C. for a further 4 hours. The mixtureis cooled to room temperature, 2 M aqueous hydrochloric acid (40 ml) isadded, and the mixture is stirred vigorously for 15 minutes, thenfiltered through a small plug of diatomaceous earth, washing with 40 mldichloromethane. The organic phase is separated, and the aqueous phaseis extracted with dichloromethane (2×20 ml). The organic solutions arecombined, dried over anhydrous magnesium sulfate, filtered and thefiltrate is concentrated under reduced pressure. The residue is purifiedby column chromatography on silica gel to give(1RS,2SR,6RS,7SR)-4-(4-bromo-2-ethylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]decane-3,5-dione.

¹H NMR (400 MHz, CDCl₃) δ_(H) 7.39 (1H, dd), 7.27-7.33 (1H, m), 6.97(1H, dd), 4.68 (2H, m), 2.74 (2H, br. s), 2.48 (2H, q), 1.78-1.87 (2H,m), 1.56 (2H, m), 1.11 (3H, t).

Additional compounds in Table T1 below were prepared by similar methodsusing appropriate starting materials. It should be noted that certaincompounds of the invention exist as a mixture of isomers noted above,under the conditions used to obtain the ¹H NMR data. Where this hasoccurred, the characterising data are reported for all isomers presentat ambient temperature in the specified solvent. Unless otherwisestated, proton NMR spectra were recorded at ambient temperature.Compounds characterised by HPLC-MS were analysed using one of twomethods described below.

Method A

Compounds characterised by HPLC-MS were analysed using an Waters 2777injector with a 1525 micro pump HPLC equipped with a Waters AtlantisdC18 IS column (column length 20 mm, internal diameter of column 3 mm,particle size 3 micron), Waters 2996 photodiode array, Waters 2420 ELSDand Micromass ZQ2000. The analysis was conducted using a three minuterun time, according to the following gradient table:

Time Solvent A Solvent B (mins) (%) (%) Flow (ml/mn) 0.00 95.0 5 1.3002.50 0.0 100 1.300 2.80 0.00 100 1.300 2.90 95.0 5 1.300 Solvent A: H₂Owith 0.05% TFA Solvent B: CH₃CN with 0.05% TFAMethod B

Compounds characterised by HPLC-MS were analysed using a Waters 2795HPLC equipped with a Waters Atlantis dC18 column (column length 20 mm,internal diameter of column 3 mm, particle size 3 micron, temperature40° C.), Waters photodiode array and Micromass ZQ2000. The analysis wasconducted using a three minute run time, according to the followinggradient table:

Time Solvent A Solvent B Flow (mins) (%) (%) (ml/mn) 0.00 90.0 10.0 2.000.25 90.0 100 2.00 2.00 10.0 90.0 2.00 2.50 10.0 90.0 2.00 2.60 90.010.0 2.00 3.0 90.0 10.0 2.00 Solvent A: H₂O containing 0.1% HCOOHSolvent B: CH₃CN containing 0.1% HCOOH

The characteristic values obtained for each compound were the retentiontime (rt, recorded in minutes) and the molecular ion (typically thecation MH⁺), as listed in Table T1.

TABLE T1 Compound ¹H nmr (CDCl₃ unless stated) or other physical NumberStructure data T1

δ_(H) 6.88-6.87 (2H, m), 4.55-4.54 (2H, m), 2.62 (2H, s), 2.36-2.27 (7H,m), 1.69-1.67 (2H, m), 1.40-1.39 (2H, m), 1.03 (6H, q). T2

δ_(H) 6.88 (2H, m), 4.58 (2H, s), 2.65 (2H, m), 2.38- 2.32 (2H, m), 2.26(3H, s), 2.02 (3H, s), 1.76- 1.71 (2H, m), 1.45 (2H, m), 1.04 (3H, q).T3

δ_(H) 6.86 (1H, s), 6.85 (1H, s), 4.68-4.67 (2H, m), 2.74 (2H, s), 2.24(3H, s), 2.10 (3H, s), 2.08 (3H, s), 1.83-1.80 (2H, m), 1.56-1.54 (2H,m). T4

δ_(H) 6.94 (2H, s), 6.44 (2H, s), 5.04 (2H, s), 2.81- 2.73 (2H, m),2.41-2.35 (4H, m), 2.30 (3H, s), 1.10-1.02 (6H, m). T5

δ_(H) 6.94 (1H, s), 6.93 (1H, s), 4.64-4.63 (2H, m), 2.73 (2H, s), 2.59(2H, q), 2.41-2.31 (4H, m), 1.77 (2H, m), 1.48 (2H, m), 1.22 (3H, t),1.06 (6H, m). T6

δ_(H) 6.98 (1H, s), 6.97 (1H, s), 2.64-2.59 (2H, brs), 2.25 (3H, s),2.03 (6H, s), 1.66 (4H, s), 1.50 (6H br s). T7

δ_(H) 6.95 (1H, s), 6.47 (1H, br s), 3.00 (1H, d), 2.68- 2.66 (1H, m),2.44-2.31 (7H, m), 1.77-1.71 (4H, m), 1.58 (3H, s), 1.55 (3H, s), 1.08(6H, q). T8

δ_(H) 6.95 (s), 4.69 (d), 4.64 (d), 3.05 (d), 2.91 (d), 2.81 (d), 2.59(d), 2.44-2.32 (m), 2.31 (s), 2.00- 1.93 (m), 1.67-1.62 (m), 1.61 (s),1.58 (s), 1.10- 1.05 (m). T9

δ_(H) 6.92 (2H, s), 6.47 (1H, s), 6.32 (0.5H, s), 6.28 (0.5H, s), 5.14(0.5H, s), 4.97 (0.5H, br s), 3.06 (0.5H, br s), 2.86 (0.5H, s),2.80(0.5H br s), 2.50 (0.5H, br s), 2.28 (3H, s), 2.12 (6H, s), 1.70(3H, br s). T10

δ_(H) 6.95 (2H, s), 4.75 (2H, br), 3.40 (2H, br), 2.45 (2H, q), 2.35(2H, q), 2.30 (3H, s), 1.80 (4H, m), 1.15 (3H, t), 1.05 (3H, t). T11

δ_(H) 6.70 (2H, s), 6.24 (1H, s), 4.79 (1H, s), 4.73 (1H, s), 2.67 (1H,br s), 2.56 (1H, d), 2.17-2.08 (7H, m), 0.87-0.77 (6H, m), 0.00 (9H, s).T12

δ_(H) 6.94 (2H, s), 6.66 (0.5H, s), 6.62 (0.5H, s), 5.14- 5.02 (2H, m),3.42 (1H, s), 3.10(0.5H, s), 3.00 (0.5H, s), 2.86 (0.5H, s), 2.77 (0.5H, s), 2.38- 2.31 (7H, m), 1.10-1.01 (6H, m). T13

δ_(H) 6.95 (2H, s), 6.60 (1H, s), 6.53-6.51 (1H, m), 5.07 (1H, s),4.14-4.00 (2H, m), 3.10-2.90 (br m, 2H), 2.42-2.28 (7H, m), 1.11-1.04(6H, m). T14

δ_(H) 6.88 (2H, s), 4.57 (1H, d), 3.86 (1H, d), 3.73 (1H, d), 3.23 (1H,s), 2.35-2.27 (7H, m), 1.86- 1.53 (4H, m), 1.06-1.00 (6H, m). T15

δ_(H) 6.94 (1H, s), 6.93 (1H, s), 4.86 (1H, s), 4.79 (1H, d), 4.76 (1H,s), 3.50 (1H, d), 2.96 (1H, s), 2.78 (1H, s), 2.50-2.25 (9H, m),1.24-1.18 (3H, m), 1.09-1.02 (6H, m). T16

δ_(H) 6.92 (2H, s), 5.00 (1H, d), 4.96 (1H, s), 4.93 (1H, s), 4.37-4.32(2H, m), 3.78 (1H, d), 2.96 (1H, s), 2.61 (1H, s), 2.34-2.30 (7H, m),1.39- 1.35 (3H, m), 1.07-1.00 (6H, m). T17

δ_(H) 8.40 (1H, s), 6.93 (1H, s), 6.92 (1H, s), 4.78 (1H, d), 4.01 (1H,d), 3.75 (1H, d), 3.52 (3H, s), 3.11 (1H, d), 2.81 (1H, d), 2.44-2.31(4H, m), 2.30 (3H, s), 2.00-1.93 (2H, m), 1.75-1.70 (2H, m), 1.09-1.05(6H, m). T18

δ_(H) 6.88 (1H, s), 6.87 (1H, s), 4.66 (1H, d), 3.94 (1H, d), 3.77 (1H,d), 3.65-3.52 (2H, m), 2.88 (1H, s), 2.80 (1H, d), 2.39-2.26 ((7H, m),1.94- 1.90 (2H, m), 1.65-1.60 (4H, m), 1.20 (3H, t), 1.05-1.00 (6H, m).T19

δ_(H) 6.92 (1H, s), 6.91 (1H, s), 4.75 (2H, s), 4.69 (1H, s), 4.04-3.96(2H, m), 3.64-3.61 (2H, m), 2.94 (1H, br s), 2.81 (1H, d), 2.42-2.30(4H, m), 2.30 (3H, s), 2.00-1.86 (2H, m), 1.69-1.54 (2H, m), 1.22-1.19(3H, m), 1.08-1.04 (8H, m). T20

δ_(H) 7.29-7.26 (2H, m), 7.05 (2H, d), 6.85 (1H, s), 6.84 (1H, s), 6.39(1H, d), 5.32 (1H, s), 5.02 (1H, d), 2.79-2.75 (2H, m), 2.33 (3H, s),3.23 (3H, s), 2.07 (3H, s), 2.04 (3H, s). T21

δ_(H) 6.87 (2H, s), 5.44 (1H, v. br s), 4.71-4.64 (2H, m), 4.26-4.23(1H, m), 3.11-3.06 (2H, m), 2.90 (1H, br s), 2.81 (1H, d), 2.38-2.27(4H,m), 2.25 (3H, s), 1.93-1.82 (2H, m), 1.66-1.52 (2H, m), 1.50-1.43 (2H,m), 1.01 (6H, t), 0.87 (3H, t). T22

δ_(H) 7.21 (1H, d), 6.93 (1H, dd), 6.84 (2H, s), 6.30 (1H, s), 5.24 (1H,s), 5.04 (1H, s), 2.82-2.81 (1H, m), 2.78-2.77 (1H, m), 2.28 (3H, s withfine splitting) 2.22 (3H, s), 2.07 (3H, s), 2.04 (3H, s). T23

δ_(H) 7.33 (2H, d), 6.86-6.81 (4H, m), 6.35 (1H, s), 5.32 (1H, s), 5.04(1H, s), 3.80 (3H, s), 2.83-2.82 (1H, m), 2.77 (1H, br s), 2.24 (3H, s),2.07 (3H, s), 2.05 (3H, s). T24

δ_(H) 7.35-7.32 (2H, m), 6.86 (1H, s), 6.85 (1H, s), 6.82-6.77 (2H, m),6.37 (1H, d), 5.31 (1H, s), 5.03 (1H, d), 2.82-2.78 (2H, m), 2.25 (3H,s), 2.07 (3H, s), 2.05 (3H, s). T25

δ_(H) 7.25-7.17 (4H, m), 6.86 (1H, s), 6.84 (1H, s), 4.73 (1H, d), 4.68(1H, d), 3.61-3.56 (1H, m), 2.90 (1H, d), 2.80 (1H, d), 2.35-2.20 (4H,m). 2.24 (3H, s), 2.07 (3H, s), 2.02 (3H, s), 1.92 (1H, dd). T26

δ_(H) 7.38-7.36 (2H, m), 7.22-7.20 (2H, m), 6.86 (2H, s), 6.58 (1H, d),5.38 (1H, d), 5.11 (1H, s), 2.90 (1H, m), 2.84(1H, m), 2.47 (3H, s),2.24 (3H, s), 2.08 (6H, s). T27

δ_(H) 6.92 (2H, s), 4.62 (1H, d), 4.29-4.27 (1H, m), 4.10-4.03 (2H, m),3.93-3.90 (1H, m), 2.84 (1H, d), 2.77 (1H, d), 2.38-2.29 (4H, m), 2.30(3H, s), 1.96-1.88 (2H, m), 1.59-1.51 (2H, m), 1.07- 1.03 (6H, m). T28

δ_(H) 7.39 (2H, dd), 7.11 (2H, t), 6.86 (1H, s), 6.85 (1H, s), 4.73 (1H,d), 4.68 (1H, d), 3.63-3.58 (1H, m), 2.94 (1H, d), 2.75 (1H, d),2.38-2.30 (1H, m), 2.25 (3H, s), 2.08 (3H, s), 2.03 (3H, s), 1.92 (1H,dd). T29

δ_(H) 6.82 (2H, s), 4.54 (1H, d), 3.85 (1H, d), 3.67 (1H, d), 3.30 (3H,s), 2.90 (1H, d), 2.78 (1H, d), 2.20 (3H, s), 2.03 (3H, s), 1.99 (3H,s), 1.93 (1H, dd), 1.87-1.81 (1H, m), 1.70-1.63 (1H, m), 1.58- 1.54 (1H,m). T30

δ_(H) 6.87 (1H, s), 6.86 (1H, s), 4.87-4.81 (1H, m), 4.67-4.65 (1H, m),4.08-3.93 (2H, m), 3.66- 3.58 (2H, m), 2.89-2.84 (1H, m), 2.76-2.73 (1H,m), 2.25 (3H, s), 2.09 (3H, s), 2.06 (3H, s), 1.95- 1.84 (2H, m),1.71-1.59 (2H, m), 1.26-1.17 (3H, m). T31

δ_(H) 6.88 (1H, s), 6.87 (1H, s), 4.67 (1H, t), 3.97 (1H, d), 3.81 (1H,d), 3.70-3.62 (1H, m), 3.60- 3.54 (1H, m), 2.87-2.82 (2H, m), 2.25 (3H,s), 2.10 (3H, s), 2.06 (3H, s), 1.99-1.94 (2H, m), 1.69-1.64 (2H, m),1.23 (3H, t). T32

δ_(H) 7.20-7.18 (2H, m), 7.12-7.10(2H, m), 6.88 (1H, s), 6.85 (1H, s),4.71 (2H, t), 3.55-3.50 (1H, m), 2.77(1H, d), 2.73 (1H, d), 2.48 (3H,s), 2.32- 2.25 (1H, m), 2.23 (3H, s), 2.07 (3H, s), 2.01 (3H, s), 1.72(1H, dd). T33

δ_(H) 6.93 (2H, s), 6.88 (2H, s), 6.36 (1H, d), 5.13 (1H, d), 5.01 (1H,s), 3.13 (1H, d), 2.96 (1H, d), 2.29 (12H, s), 2.11 (3H, s), 2.09 (3H,s). T34

δ_(H) 2.82 (2H, s), 6.19 (2H, s), 2.51 (2H, br s), 2.22 (3H, s), 2.05(3H, s), 2.04 (3H, s), 1.57 (6H, s). T35

δ_(H) 6.88 (1H, s), 6.87 (1H, s), 4.73-4.69 (2H, m), 4.29 (1H, d),3.14-3.09 (2H, m), 2.93 (1H, d), 2.85 (1H, d), 2.25 (3H, s), 2.09 (3H,s), 2.06 (3H, s), 1.97-1.86 (2H, m), 1.71-1.59 (2H, m), 1.54- 1.47 (2H,m), 0.91 (3H, t). T36

δ_(H) 6.83 (2H, s), 5.02 (1H, s), 4.72 (1H, d), 4.65 (1H, d), 4.12 (1H,d), 2.83 (1H, d), 2.70 (1H, d), 2.23 (3H, s), 2.07 (3H, s), 2.06 (3H,s), 1.86-1.80 (2H, m), 1.57-1.45 (2H, m), 1.29 (9H, s). T37

LC-MS (Method A) ES⁺: MH⁺ = 313; rt = 1.07 mins T38

LC-MS (Method A) ES⁺: MH⁺ = 313; rt = 1.07 mins T39

LC-MS (Method A) ES⁺: MH⁺ = 327; rt = 1.23 mins T40

LC-MS (Method A) ES⁺: MH⁺ = 311; rt = 1.34 mins T41

LC-MS (Method A) ES⁺: MH⁺ = 343; rt = 1.35 mins T42

LC-MS (Method A) ES⁺: MH⁺ = 353; rt = 1.79 mins T43

LC-MS (Method A) ES⁺: MH⁺ = 371; rt = 1.50 mins T44

LC-MS (Method A) ES⁺: MH⁺ = 297; rt = 1.25 mins T45

δ_(H) 6.86 (2H, s), 4.61-4.58 (2H, m), 4.43 (1H, d), 4.07 (1H, d), 3.95(1H, d), 2.98-2.85 (2H, m), 2.24 (3H, s), 2.08 (3H, s), 2.06 (3H, s),1.91-1.87 (2H, m), 1.76-1.70 (1H, m), 1.65-1.59 (1H, m). T46

δ_(H) 6.93 (2H, s), 4.75 (1H, d), 4.72 (1H, s), 4.38 (1H, dd), 3.93 (1H,d), 3.68 (1H, d), 2.90 (1H, d), 2.38-2.31 (7H, m), 1.08-1.01 (6H, m).T47

δ_(H) 6.82 (2H, s), 4.50-4.45 (2H, m), 3.36-3.34 (1H, m), 3.26-3.24 (4H,m), 2.92 (1H, d), 2.47 (1H, d), 2.41-2.36 (1H, m), 2.23 (3H, s), 2.02(6H, s), 1.95-1.88 (1H, m), 1.00 (1H, dd). T48

δ_(H) 6.84-6.83 (2H, m), 4.47 (1H, d), 2.63 (1H, d), 2.41 (1H, d), 2.23(3H, s), 2.04 (3H, s), 2.01 (3H, s), 1.86-1.83 (1H, m), 1.55-1.46 (3H,m), 1.48 (3H, s). T49

δ_(H) 6.85 (2H, s), 4.55 (1H, d), 3.84 (1H, d), 3.75 (1H, d), 2.76-2.70(2H, m), 2.23 (3H, s), 2.03 (6H, s). T50

δ_(H) 6.83-6.82 (2H, m), 4.48-4.45 (2H, m), 3.35- 3.34 (1H, m),3.26-3.24 (1H, m), 2.93 (1H, d), 2.48 (1H, d), 2.23 (3H, s), 2.02 (6H,s), 2.42- 2.36 (1H, m), 1.94-1.88 (1H, m), 1.01 (1H, dd). T51

δ_(H) 6.85 (2H, s), 4.55 (1H, d), 4.03 (1H, q), 2.76 (1H, d), 2.72 (1H,d), 2.23 (3H, s), 2.04 (3H, s), 2.03 (3H, s), 1.84-1.70 (2H, m),1.58-1.41 (2H, m), 1.24 (3H, d). T52

δ_(H) 6.82 (1H, s), 6.81 (1H, s), 4.42 (1H, d), 2.53- 2.48 (2H, m), 2.22(3H, s), 2.00 (3H, s), 1.98 (3H, s), 1.93-1.86 (1H, m), 1.77-1.70 (2H,m), 1.54- 1.41 (3H, m), 1.03 (3H, t). T53

δ_(H) 6.83 (2H, s), 4.49 (1H, d), 3.00-2.92 (2H, m), 2.62-2.58 (2H, m),2.23 (3H, s) ,2.14 (3H, s), 2.02 (3H, s), 2.00 (3H, s), 2.00-1.85 (2H,m), 1.52-1.47 (2H, m). T54

δ_(H) 6.84 (1H, s), 6.83 (1H, s), 4.45 (1H, d), 2.60- 2.56 (2H, m), 2.23(3H, s), 2.04 (3H, s), 2.00 (3H, s), 1.93-1.88 (1H, m), 1.80-1.76 (1H,m), 1.69- 1.46 (4H, m), 1.35-1.26 (6H, m), 0.88-0.85 (3H, m). T55

δ_(H) 6.86 (2H, m), 3.11-3.00 (4H, m), 2.72 (1H, d), 2.25 (3H, s), 2.09(3H, s), 2.05 (3H, s), 1.98- 1.89 (1H, m), 1.79-1.56 (3H, m), 1.33-1.25(6H, m). T56

δ_(H) 7.28-7.17 (5H, m), 6.89 (1H, s), 6.88 (1H, s), 4.72 (1H, d), 4.53(1H, s), 2.89 (1H, dd), 3.02 (1H, d), 2.96 (1H, d), 2.32-2.30 (1H, m),2.27 (3H, s), 2.07 (6H, s), 1.90-1.85 (1H, m). T57

δ_(H) 7.26-7.23 (2H, m), 6.88-6.85 (4H, m), 4.74 (1H, d), 4.40 (1H, s),3.79 (3H, s), 3.10 (1H, dd), 3.02 (1H, d, 2.96 (1H, d), 2.32-2.30 (1H,m), 2.27 (3H, s), 2.07 (6H, s), 1.90-1.85 (1H, m). T58

LC-MS (Method A) ES⁺: MH⁺ = 327; rt = 1.10 mins T59

LC-MS (Method A) ES⁺: MH⁺ = 369; rt = 1.33 mins T60

LC-MS (Method A) ES⁺: MH⁺ = 365; rt = 1.77 mins T61

LC-MS (Method A) ES⁺: MH⁺ = 383; rt = 1.36 mins T62

δ_(H) 6.86 (2H, s), 4.48 (1H, d), 3.68-3.48 (2H, m), 2.81-2.74 (1H, m),2.67 (1H, d), 2.23 (3H, s), 2.07 (3H, s), 2.04 (3H, s), 1.54 (3H, s),1.27- 1.26 (1H, m), 1.04-1.01 (2H, m). T63

LC-MS (Method A) ES⁺: MH⁺ = 355; rt = 1.36 mins T64

LC-MS (Method A) ES⁺: MH⁺ = 343; rt = 1.37 mins T65

d₄-MeOH δ_(H) = 6.85 (2H, m), 4.51 (1H, d), 4.37 (1H, d), 3.14 (1H, d),2.84 (1H, d), 2.28-2.24 (1H, m), 2.24 (3H, s), 2.13 (1H, dd), 2.04 (3H,s), 2.03 (3H, s), 1.13 (3H, d), 1.11-1.06 (1H, m). T66

δ_(H) 7.26-7.18 (4H, m), 6.85 (2H, s), 4.72 (1H, d), 4.40 (1H, s), 3.09(1H, dd), 3.00 (1H, d), 2.94 (1H, d), 2.44 (3H, s), 2.29-2.24 (1H, m),2.24 (3H, s), 2.05 (6H, s), 1.88-1.82 (1H, m). T67

δ_(H) 7.24-7.21 (1H, m), 6.94-6.93 (2H, m), 6.88 (2H, s), 4.75 (1H, d),4.45 (1H, s), 3.52 (1H, dd), 3.05 (1H, d), 2.96 (1H, d), 2.35-2.29 (1H,m), 2.27 (3H, s), 2.08 (6H, s), 2.01-1.95 (1H, m). T68

Approximately 3:2 Mixture of Isomer A:Isomer B Isomer A: δ_(H) 6.86 (1H,s), 6.85 (1H, s), 4.55 (1H, d), 4.53 (1H, d), 3.50-3.42 (3H, m),3.36-3.33 (1H, m), 3.02 (1H, d), 2.49-2.43 (2H, m), 2.25 (3H, s), 2.05(6H, s), 2.01-1.94 (1H, m), 1.19 (3H, t), 1.06 (1H, dd).

T69

δ_(H) 6.85 (2H, s), 4.69(2H, s), 4.56-4.54 (2H, m), 3.76-3.55 (5H, m),3.12 (1H, d), 2.83 (1H, d), 2.55-2.45 (1H, m), 2.24 (3H, s), 2.04 (3H,s), 1.24-1.15 (4H, m). T70

δ_(H) 7.34-7.31 (2H, m), 7.00 (2H, t), 6.85 (2H, s), 4.73 (1H, d), 4.39(1H, s), 3.13 (1H, dd), 3.01 (1H, d), 2.95 (1H, d), 2.30-2.27 (1H, m),2.24 (3H, s), 2.05 (6H, s), 1.87-1.81 (1H, m). T71

δ_(H) 7.21 (2H, d), 7.11 (2H, d), 6.88 (2H, s), 4.74 (1H, d), 4.42 (1H,s), 3.09 (1H, dd), 3.02 (1H, d), 2.96 (1H, d), 2.32 (3H, s), 2.29-2.24(1H, m), 2.27 (3H, s), 2.08 (6H, s), 1.91-1.85 (1H, m). T72

δ_(H) 7.25-7.18 (4H, m), 6.86 (1H, s), 6.84 (1H, s), 4.73 (1H, d), 4.68(1H, d), 3.61-3.56 (1H, m), 2.90 (1H, d), 2.80 (1H, d), 2.35 (3H, s),2.32-2.28 (1H, m), 2.24 (3H, s), 2.07 (3H, s), 2.02 (3H, s), 1.92 (1H,dd). T73

δ_(H) 7.29-7.27 (3H, m), 7.22-7.19 (2H, m), 6.89 (1H, s), 6.88 (1H, s),4.85 (1H, d), 4.61 (1H, s), 3.01 (1H, dd), 2.26 (3H, s), 2.19 (1H, dd),2.10 (3H, s), 2.09 (3H, s), 2.00-1.96 (1H, m). T74

δ_(H) 6.90 (1H, s), 6.88 (1H, s), 6.86-6.82 (2H, m), 4.82-4.77 (2H, m),3.12-3.05 (2H, m), 2.28- 2.86 (1H, m), 2.41-2.39 (1H, m), 2.26 (3H, s),2.23 (3H, s), 2.11 (6H, s), 2.08 (3H, s), 2.01-1.97 (1H, m). T75

δ_(H) 7.79-7.76 (1H, m), 7.59-7.56 (1H, m), 7.28- 7.20 (2H, m), 6.90(1H, s), 6.89 (1H, s), 4.88- 4.86 (1H, m), 4.67 (1H, s), 3.47-3.42 (1H,m), 3.14-3.00 (2H, m), 2.26 (3H, s), 2.25-2.21 (1H, m), 2.11 (3H, s),2.09 (3H, s), 1.88-1.84 (1H, m). T76

δ_(H) 7.39-7.35 (1H, m), 7.19-7.16 (1H, m), 6.93- 6.83 (4H, m), 4.82(1H, brs), 4.62 (1H, s), 3.48 (3H, s), 3.54 (1H, dd), 3.13-3.02 (2H,brm), 2.26 (3H, s), 2.17-2.13 (1H, m), 2.10 (3H, s), 2.09 (3H, s),1.90-1.84 (1H, m). T77

δ_(H) 7.42 (1H, d), 7.21-7.12 (3H, m), 6.88 (1H, s), 6.87 (1H, s), 4.82(1H, s), 4.82 (1H, d), 4.68 (1H, s), 3.51 (1H, dd), 2.47 (3H, s), 2.25(3H, s), 2.23- 2.20 (1H, m), 2.10 (3H, s), 2.08 (3H, s), 1.85- 1.81 (1H,m). T78

δ_(H) 7.73-7.70 (2H, m), 7.59 (1H, d), 7.52-7.50 (1H, m), 7.31-7.28 (1H,m), 6.89 (1H, s), 6.88 (1H, s), 4.86 (1H, br S), 4.64 (1H, s), 3.42 (1H,br S), 3.13-3.05 (2H, m), 2.26 (3H, s), 2.66-2.24 (1H, m), 2.11 (3H, s),2.08 (3H, s), 1.92-1.88 (1H, m). T79

δ_(H) 7.42-7.39 (1H, m), 7.18-7.11 (3H, m), 6.91 (1H, s), 6.90 (1H, s),4.87-4.85 (1H, m), 4.74 (1H, s), 3.24-3.22 (1H, m), 3.13-3.07 (2H, m),2.36 (3H, s), 2.34 (3H, s), 2.24-2.22 (1H, m), 2.19 (3H, s), 2.09 (3H,s), 1.88-186 (1H, m). T80

δ_(H) 7.79-7.73 (2H, m), 7.56 (1H, t), 7.35 (1H, t), 6.90 (1H, s), 6.89(1H, s), 4.87 (1H, br s), 4.71 (1H, s), 3.47 (1H, br. s), 3.13-3.06 (2H,m), 2.42- 2.30 (1H, m), 2.26 (3H, s), 2.11 (3H, s), 2.09 (3H, s),1.98-1.97 (1H, m). T81

δ_(H) 7.45-7.43 (1H, m), 7.18-7.16 (1H, m), 7.11- 7.08 (1H, m),7.02-6.98 (1H, m), 6.89 (1H, s), 6.88 (1H, s), 4.85 (1H, d), 4.65 (1H,s), 3.44 (1H, br. s), 3.15-3.00 (2H, br. s), 2.26 (3H, s), 2.22- 2.17(1H, m), 2.10 (3H, s), 2.09 (3H, s), 1.92- 1.88 (1H, s) T82

δ_(H) 7.47-7.96 (2H, m), 7.14-7.11 (2H, m), 6.90 (2H, s), 4.88 (1H, s),4.57 (1H, s), 3.21 (1H, s), 2.94-2.74 (2H, br. s), 2.62, (3H, s), 2.26(3H, s), 2.25-2.23 (1H, m), 2.11 (3H, s), 2.10 (3H, s), 2.01-1.93 (1H,m). T83

δ_(H) 7.75-7.66 (1H, m), 7.25-7.21 (1H, m), 7.06- 7.02 (2H, m), 6.88(1H, s), 6.87 (1H, s), 4.83 (1H, br. s), 4.59 (1H, s), 3.00-2.98 (1H,m), 2.83- 2.70 (2H, br. s), 2.25 (3H, s), 2.20-2.16 (1H, m), 2.09 (3H,s), 2.08 (3H, s), 1.92-1.89 (1H, m). T84

δ_(H) 7.79-7.77 (1H, m), 7.21-7.18 (1H, m), 6.89- 6.86 (3H, m),6.76-6.74 (1H, m), 4.83 (1H, d), 4.62 (1H, s), 3.80 (3H, s), 2.99 (1H,dd), 2.80- 2.70 (2H, br. s), 2.26 (3H, s), 2.18 (1H, dd), 2.10 (3H, s),2.09 (3H, s), 1.97-1.95 (1H, m). T85

δ_(H) 7.54-7.46 (3H, m), 7.41-7.38 (1H, m), 6.87 (1H, s), 6.88 (1H, s),4.85 (1H, d), 4.60 (1H, s), 3.06 (1H, dd), 2.25 (3H, s), 2.21 (1H, dd),2.10 (3H, s), 2.08 (3H, s), 1.93-1.90 (1H, m). T86

δ_(H) 7.19-7.08 (3H, m), 7.03-7.07 (1H, m), 6.89 (1H, s), 6.88 (1H, s),4.84 (1H, d), 4.60 (1H, s), 2.98 (1H, dd), 2.33 (3H, s), 2.26 (3H, s),2.17 (1H, dd), 2.10 (3H, s), 2.08 (3H, s), 1.97-1.95 (1H, br. m). T87

δ_(H) 8.09-8.07 (1H, m), 7.68-7.67 (2H, m), 7.46 (1H, t), 6.89 (1H, s),6.88 (1H, s), 4.89 (1H, d), 4.62 (1H, s), 3.13 (1H, dd), 2.28-2.24 (1H,m), 2.25 (3H, s), 2.10 (3H, s), 2.08 (3H, s), 1.95-1.95 (1H, m). T88

δ_(H) 7.88-7.86 (1H, m), 7.79 (1H, d), 7.55-7.53 (1H, m), 7.39 (1H, t),6.88 (1H, s), 6.87 (1H, s), 4.87 (1H, d), 4.61 (1H, s), 3.09 (1H, dd),2.60 (3H, s), 2.25 (3H, s), 2.23-2.20 (1H, m), 2.10 (3H, s), 2.08 (3H,s), 1.96-1.94 (1H, m). T89

δ_(H) 7.62-7.60 (1H, m), 7.56-7.50 (2H, m), 7.39 (1H, t), 6.90 (1H, s),6.88 (1H, s), 4.88 (1H, br. s), 4.59 (1H, s), 3.05-3.03 (1H, m), 2.26(3H, s), 2.24- 2.20 (1H, m), 2.10 (3H, s), 2.08 (3H, s), 1.92- 1.89 (1H,m). T90

δ_(H) 8.14 (2H, d), 7.47 (2H, d), 6.89 (1H, s), 6.87 (1H, s), 4.89 (1H,d), 4.63 (1H, s), 3.12 (1H, dd), 2.27-2.23 (1H, m), 2.26 (3H, s), 2.10(3H, s), 2.08 (3H, s), 1.95-1.91 (1H, m). T91

δ_(H) 7.35-7.31 (2H, m), 7.15-7.12 (2H, m), 6.91 (1H, s), 6.90 (1H, s),4.87 (1H, br. s), 4.61 (1H, s), 3.07-3.05 (1H, m), 2.27 (3H, s),2.22-2.20 (1H, m), 2.10 (3H, s), 2.09 (3H, s), 1.93-1.91 (1H, m). T92

δ_(H) 7.54 (2H, d), 7.43-7.41 (2H, m), 6.89 (1H, s), 6.88 (1H, s), 4.87(1H, d), 4.61 (1H, s), 3.07 (1H, dd), 2.26 (3H, s), 2.23 (1H, dd), 2.10(3H, s), 2.08 (3H, s), 1.95-1.91 (1H, m). T93

δ_(H) 7.57 (2H, d), 7.41 (2H, d), 6.88 (1H, s), 6.87 (1H, s), 4.86 (1H,d), 4.60 (1H, s), 3.05 (1h, dd), 2.25 (3H, s), 2.23-2.20 (1H, m), 2.09(3H, s), 2.08 (3H, s), 1.95-1.91 (1H, m). T94

δ_(H) 7.31-7.29 (2H, m), 7.24-7.22 (2H, m), 6.89 (1H, s), 6.88 (1H, s),4.85 (1H, d), 4.59 (1H, s), 3.00 (1H, dd), 2.26 (3H, s), 2.17 (1H, dd),2.10 (3H, s), 2.09 (3H, s), 1.99-1.96 (1H, m), 1.30 (9H, s). T95

δ_(H) 7.88 (2H, d), 7.41-7.38 (2H, m), 6.90 (1H, s), 6.88 (1H, s), 4.88(1H, br. s), 4.63 (1H, s), 3.08 (1H, br. s), 2.58 (3H, s), 2.26 (3H, s),2.23-2.21 (1H, m), 2.11 (3H, s), 2.09 (3H, s), 1.95-1.93 (1H, m). T96

LC-MS (Method A) ES⁺: MH⁺ = 428; rt = 1.52 mins T97

δ_(H) 6.85 (2H, s), 4.50 (1H, d), 4.37 (1H, d), 3.31- 3.29 (1H, m), 3.12(1H, d), 2.81 (1H, d), 2.24 (3H, s), 2.14-2.07 (1H, m), 2.05 (3H, s),2.03 (3H, s), 1.12 (3H, d), 1.07 (1H, dd). T98

δ_(H) 7.33-7.18 (5H, m), 6.84-6.81 (2H, m), 6.35 (1H, d), 6.08 (1H, dd),4.63 (1H, d), 4.42 (1H, s), 2.68-2.63 (2H, m), 2.55-2.48 (1H, m), 2.22(3H, s), 2.04 (3H, s), 2.02 (3H, s), 1.85-1.80 (1H, m), 1.64-1.60 (1H,m). T99

δ_(H) 6.90-6.89 (2H, m), 5.80-5.71 (1H, m), 5.05- 4.97 (2H, m), 4.68(1H, d), 4.44 (1H, s), 2.81- 2.76 (2H, m), 2.51-2.46 (1H, m), 2.26 (3H,s), 2.07 (3H, s), 2.06 (3H, s), 1.89-1.84 (1H, m), 1.67-1.62 (1H, m).T100

δ_(H) 7.27-7.12 (6H, m), 6.83 (2H, br. s), 4.55 (1H, d), 4.33 (1H, s),2.75-2.71 (2H, m), 2.64 (2H, t), 2.23 (3H, s), 2.04 (6H, s), 1.74-1.68(3H, m), 1.57-1.50 (1H, m), 1.44-1.41 (1H, m). T101

δ_(H) 6.87 (2H, s), 6.40 (1H, d), 4.95 (1H, s), 4.82 (1H, s), 2.90 (1h,d), 2.81 (1H, d), 2.25 (3H, s), 2.07 (3H, s), 2.03 (3H, s). T102

δ_(H) 6.82 (2H, s), 4.47 (1H, d), 4.25 (1H, s), 2.50- 2.46 (2H, m), 2.22(3H, s), 2.02 (3H, s), 2.01 (3H, s), 1.69-1.50 (4H, m), 1.34-1.12 (6H,m), 0.88- 0.86 (6H, m). T103

δ_(H) 6.81 (2H, s), 4.47 (1H, d), 4.24 (1H, s), 3.64 (3H, s), 2.52-2.47(2H, m), 2.28-2.20 (5H, m), 2.00 (6H, s), 1.70-1.48 (H, m), 1.27-1.24(1H, m). T104

Aproximately 85:15 mixture of E- and Z- isomers. E-isomer: δ_(H) 6.84(2H, s), 5.42-5.26 (2H, m), 4.53 (1H, d), 4.29 (1H, s), 2.58 (1H, m),2.37-2.29 (1H, m), 2.23 (3H, s), 2.02 (3H, s), 2.01 (3H, s), 1.86-1.83(2H, m), 1.75-1.70 (1H, m), 1.63-1.47 (3H, m) ,0.89-0.86 (6H, m). T105

Approximately 3:2 mixture of E- and Z-isomers. E-isomer δ_(H) 6.80 (2H,s), 6.74 (1H, dd), 5.91 (1H, d), 4.58 (1H, d), 4.30 (1H, s), 3.33 (3H,s), 2.85- 2.77 (3H, m), 2.21 (3H, s), 1.97 (3H, s), 194 (3H, s),1.94-1.91 (1H, m), 1.59-1.54 (1H, m). T106

δ_(H) 6.82 (2H, s), 4.44 (1H, d), 4.24 (1H, s), 2.45- 2.40 (2H, m), 2.22(3H, s), 2.02 (6H, s), 1.58- 1.52 (2H, m), 1.38-1.33 (1H, m), 1.25-1.16(2H, m), 0.85-0.82 (3H, m). T107

δ_(H) 6.85 (2H, s), 4.51 (1H, d), 4.43 (1H, d), 3.07 (1H, d), 2.82-2.81(1H, m), 2.24 (3H, s), 2.10- 2.05 (2H, m), 2.04 (6H, s), 1.87-1.79 (1H,m), 1.53-1.46 (2H, m), 1.00 (3H, t). T108

δ_(H) 8.82 (1H, s), 8.76 (1H, d), 8.03 (1H, dd), 6.82 (2H, s), 4.90 (1H,d), 4.63 (1H, s), 3.55 (1H, dd), 3.16 (1H, d), 3.08 (1H, d), 2.46-2.40(1H, m), 2.23 (3H, s), 2.08 (6H, s), 2.02-1.96 (1H, m). T109

LC-MS (Method A) ES⁺: MH⁺ = 327; rt = 4.97 mins T110

LC-MS (Method A) ES⁺: MH⁺ = 369; rt = 4.98 mins T111

LC-MS (Method A) ES⁺: MH⁺ = 412; rt = 5.70 mins T112

LC-MS (Method A) ES⁺: MH⁺ = 435; rt = 4.23 mins T113

LC-MS (Method A) ES⁺: MH⁺ = 353; rt = 4.48 mins T114

LC-MS (Method A) ES⁺: MH⁺ = 371; rt = 5.23 mins T115

LC-MS (Method A) ES⁺: MH⁺ = 325; rt = 4.22 mins T116

LC-MS (Method A) ES⁺: MH⁺ = 371; rt = 5.51 mins T117

LC-MS (Method A) ES⁺: MH⁺ = 431; rt = 4.98 mins T118

LC-MS (Method A) ES⁺: MH⁺ = 381; rt = 7.34 mins T119

LC-MS (Method A) ES⁺: MH⁺ = 339, rt = 6.54 mins T120

LC-MS (Method A) ES⁺: MH⁺ = 353; rt = 5.23 mins T121

LC-MS (Method A) ES⁺: MH⁺ = 407; rt = 5.04 mins T122

LC-MS (Method B) ES⁺: MH⁺ = 329; rt = 1.18 mins T123

LC-MS (Method B) ES⁺: MH⁺ = 355; rt = 1.32 mins T124

LC-MS (Method B) ES⁺: MH⁺ = 43; rt = 1.58 mins T125

LC-MS (Method B) ES⁺: MH⁺ = 327; rt = 1.45 mins T126

LC-MS (Method B) ES⁺: MH⁺ = 383; rt = 1.93 mins T127

d₄-MeOH δ_(H) 6.84 (2H, s), 4.50 (2H, s), 3.56 (2H, s), 2.88 (2H, s),2.23 (3H, s), 2.05 (3H, s), 2.02 (3H, s). T128

d₄-MeOH δ_(H) 8.68 (1H, d), 8.03 (1H, dd), 7.78 (1H, d), 6.89 (2H, s),4.83 (1H, d), 4.52 (1H, s), 3.36- 3.34 (1H, m), 3.10 (1H, d), 3.03 (1H,d), 2.83 (1H, dd), 2.27 (3H, s), 2.09 (3H, s), 2.08 (3H, s), 1.93- 1.88(1H, m). T129

d₄-MeOH δ_(H) 8.10 (1H, d), 7.95-7.90 (1H, m), 7.00 (1H, dd), 6.85 (2H,s), 4.77 (1H, d), 4.41 (1H, s), 3.21 (1H, dd), 3.03 (1H, d), 2.96 (1H,d), 2.30 (1H, dd), 2.23 (3H, s), 2.05 (6H, s), 1.85-1.80 (1H, m). T130

d₄-MeOH δ_(H) 8.65 (1H, d), 7.97 (1H, dd), 7.81 (1H, d), 6.85 (2H, s),4.80 (1H, d), 4.48 (1H, s), 3.34- 3.31 (1H, m), 3.06 (1H, d), 2.99 (1H,d), 2.35 (1H, dd), 2.24 (3H, s), 2.05 (3H, s), 2.04 (3H, s), 1.91- 1.86(1H, m). T131

d₄-MeOH δ_(H) 8.63 (1H, d), 8.34 (1H, d), 8.22 (1H, dd), 6.92 (2H, s),4.88 (1H, d), 4.56 (1H, s), 3.48 (1H, dd), 3.14 (1H, d), 3.06 (1H, d),2.43 (1H, dd), 2.31 (3H, s), 2.12 (3H, s), 2.11 (3H, s), 2.00-1.94 (1H,m). T132

d₄-MeOH δ_(H) 7.39 (1H, dd), 7.18 (1H, d), 7.16 (1H, d), 6.35 (2H, s),2.79 (2H, s), 2.46 (2H, q), 1.61 (6H, s), 1.07 (3H, t) T133

d₄-MeOH δ_(H) 7.37 (1H, dd), 7.17 (1H, d), 7.14 (1H, d), 6.54 (2H, s),4.96 (2H, s), 2.79 (2H, s), 2.44 (2H, q), 1.06 (3H, t) T134

d₄-MeOH δ_(H) 7.34 (1H, dd), 7.15 (2H, d), 4.59 (2H, s), 2.78 (2H, s),2.43 (2H, q), 1.81-1.78 (2H, m), 1.66-1.61 (2H, m), 1.06 (3H, t) T135

d₄-MeOH δ_(H) 8.13 (1H, s), 6.80 (2H, s), 6.76 (1H, d), 5.28 (1H, s),5.06 (1H, d), 4.11 (3H, s), 2.71 (1H, d), 2.60 (1H, d), 2.21 (3H, s),2.08 (6H, s). T136

δ_(H) 6.82 (2H, s), 6.48-6.44 (2H, m), 4.98 (1H, s), 2.93-2.87 (2H, m),2.19 (3H, s), 2.05 (3H, s), 2.02 (3H, s). T137

d₄-MeOH δ_(H) 7.93 (1H, s), 6.82 (1H, s), 6.80 (1H, s), 4.72 (1H, d),4.71 (1H, d), 4.12 (3H, s), 3.59- 3.54 (1H, m), 2.76 (1H, d), 2.66 (1H,d), 2.41- 2.32 (1H, m), 2.23 (3H, s), 2.10 (3H, s), 2.06 (3H, s),2.00-1.95 (1H, m). T138

Approximately 9:1 mixture of Isomer A:Isomer B. Isomer A: d₄-MeOH δ_(H)6.83 (2H, s), 4.77 (1H, d,), 4.69 (1H, d), 3.22 (1H, d), 3.16-3.13 (1H,m), 2.85 (1H, d), 2.35-2.29 (1H, m), 2.23 (3H, s), 2.07 (3H, s), 2.03(3, s), 1.87 (1H, dd).

T139

d₆-DMSO δ_(H) 7.17 (1H, s), 7.18 (1H, s), 6.50 (2H, s), 4.86 (2H, s) 2.7(2H, br. s), 2.00 (3H, s), 1.95 (3H, s) T140

d₄-MeOH δ_(H) 6.83 (2H, s), 5.35 (1H, s), 4.64 (1H, d), 4.05-3.93 (4H,m), 2.84-2.80 (2H, m), 2.24 (3H, s), 2.10 (3H, s), 2.08 (3H, s),1.93-1.85 (2H, m), 1.73-1.68 (1H, m), 1.58-1.54 (1H, m). T141

d₄-MeOH δ_(H) 6.82 (1H, s), 6.80 (1H, s), 5.04 (1H, s), 4.62 (1H, d),3.66-3.49 (4H, m), 2.72-2.67 (2H, m), 2.23 (3H, s), 2.12 (3H, s), 2.10(3H, s), 2.11-2.08 (1H, m), 1.94-1.83 (1H, m), 1.70- 1.62 (2H, m), 1.21(3H, s), 0.74 (3H, s). T142

LC-MS (Method B) ES⁺: MH⁺ = 439; rt = 1.35 mins T143

δ_(H) 7.32 (1H, d), 7.15 (1H, s), 7.02 (1H, d), 6.91- 6.90 (2H, m),4.75-4.73 (1H, br. m), 4.62 (1H, s), 3.46-3.44 (1H, m), 2.95-2.84 (2H,m), 2.37- 2.28 (10H, m), 2.16-2.11 (1H, m), 1.76-1.73 (1H, m), 1.06-1.02(6H, m). T144

δ_(H) 7.48 (1H, s), 7.28 (1H, s), 7.13 (1H, d), 6.96- 6.94 (2H, m), 4.86(1H, s), 4.68 (1H, s), 3.52 (1H, s with fine splitting), 3.11-2.90 (2H,m), 2.40- 2.23 (8H, m), 1.83-1.80 (1H, m), 1.10-1.06 (6H, m). T145

δ_(H) 7.26-7.21 (2H, m), 7.05-7.02 (2H, m), 6.94- 6.88 (3H, m), 4.81(1H, s), 4.59 (1H, s), 2.99- 2.85 (3H, m), 2.40-2.30 (7H, m), 2.19-2.14(1H, m), 1.91-1.89 (1H, m), 1.06 (6H, t). T146

δ_(H) 7.08-7.05 (1H, m), 6.97-6.92 (4H, m), 4.80 (1H, br. s), 4.56 (1H,s), 3.10-2.82 (3H, m), 2.38- 2.33 (4H, m), 2.30 (3H, s), 2.23 (3H, s),2.18- 2.11 (1H, m), 1.90-1.86 (1H, m), 1.08-1.05 (6H, m). T147

δ_(H) 7.16-7.13 (1H, m), 7.08-7.05 (1H, m), 6.96 (1H, s), 6.94 (1H, s),6.81-6.78 (1H, m), 4.86 (1H, br. s), 4.67 (1H, s), 3.18 (1H, br. s),3.10 (1H, br. s), 2.85 (1H, br. s), 2.40-2.36 4H, m), 2.31 (3H, s), 2.28(3H, s), 2.23-2.18 (1H, m), 1.81 (1H, br. s), 1.10-1.06 (6H, m). T148

δ_(H) 7.34-7.31 (1H, m), 7.25-7.15 (3H, m), 6.96 (1H, s), 6.94 (1H, s),4.87-4.85 (1H, m), 4.65 (1H, s), 3.11-3.08 (1H, m), 3.02-2.98 (1H, m),2.86-2.80 (1H, m), 2.43-2.33 (4H, m), 2.31 (3H, s), 2.23-2.18 (1H, m),2.00-1.92 (1H, m), 1.09- 1.06 (6H, m). T149

δ_(H) 7.36 (1H, d), 7.16-7.13 (1H, m), 7.04 (1H, t), 6.95 (1H, s), 6.94(1H, s), 4.83 (1H, br. s), 4.56 (1H, s), 2.96-2.83 (3H, m), 2.39-2.35(4H, m), 2.31 (3H, s), 2.21-2.16 (1H, m), 1.88-1.85 (1H, m), 1.08-1.05(6H, m). T150

δ_(H) 7.41-7.39 (1H, m), 7.35-7.33 (1H, m), 7.12- 7.10 (1H, m), 6.94(1H, s), 6.93 (1H, s), 4.82- 4.80 (1H, m), 4.56 (1H, s), 2.98-2.80 (3H,m), 2.37-2.33 (4H, m), 2.30 (3H, s), 2.19-2.15 (1H, m), 1.87-1.83 (1H,m), 1.08-1.04 (6H, m). T151

δ_(H) 7.28 (1H, br. s), 7.13-7.11 (1H, m), 7.07-7.05 (1H, m), 6.94 (1H,s), 6.92 (1H, s), 4.79-4.78 (1H, m), 4.55 (1H, s), 2.95-2.80 (3H, m),2.39- 2.34 (4H, m), 2.33 (3H, s), 2.30 (3H, s), 2.15- 2.10 (1H, m),1.89-1.84 (1H, m), 1.07-1.04 (6H, m). T152

δ_(H) 7.22-7.18 (3H, m), 6.93 (1H, s), 6.92 (1H, s), 4.79 (1H, s), 4.56(1H, s), 2.93-2.88 (2H, m), 2.37-2.32 (6H, m), 2.29 (3H, s), 2.13 (1H,br. m), 1.85 (1H, br. m), 1.07-1.04 (6H, m). T153

δ_(H) 7.21-7.18 (1H, m), 6.94 (1H, s), 6.93 (1H, s), 6.90-6.84 (2H, m),6.76-6.74 (1H, m), 4.81 (1H, br. s), 4.60 (1H, s), 3.80 (3H, s),2.97-2.83 (2H, m), 2.83-2.35 (5H, m), 2.30 (3H, s), 2.16-2.14 (1H, m),2.00-1.96 (1H, m), 1.09-1.04 (6H, m). T154

δ_(H) 7.53-7.39 (4H, m), 6.94-6.93 (2H, m), 4.82 (1H, br. s), 4.59 (1H,d), 3.04-3.02 (1H, m), 2.93- 2.89 (2H, br. m), 2.38-2.33 (4H, m), 2.30(3H, s), 2.18 (3H, s), 2.16 (3H, s), 1.92-1.90 (1H, m), 1.08-1.04 (6H,m). T155

δ_(H) 7.26-7.25 (4H, m), 6.95-6.94 (2H, m), 4.84 (1H, s), 4.60-4.57 (1H,m), 3.09-3.06 (1H, m), 2.99-2.97 (1H, m), 2.85-2.80(1H, m), 2.40- 2.36(4H, m), 2.31 (3H, s), 2.22-2.17 (1H, m), 1.93-1.89 (1H, m), 1.09-1.05(6H, m). T156

δ_(H) 7.22-7.20 (2H, m), 6.95-6.93 (2H, m), 6.84- 6.82 (2H, m),4.83-4.82 (1H, br. m), 4.56 (1H, s), 3.78 (3H, s), 2.98-2.95 (1H, m),2.90-2.75 (2H, br. s), 2.39-2.35(4H, m), 2.30(3H, s), 2.19- 2.13 (1H,m), 1.95-1.89 (1H, m), 1.09-1.05 (6H, m). T157

δ_(H) 7.57-7.53 (1H, m), 7.44-7.42 (1H, m), 7.09- 7.05 (1H, m), 6.93(2H, s), 4.84 (1H, br. s), 4.70 (1H, br. s), 3.45-3.33 (1H, m),3.10-2.90 (2H, m), 2.37-2.32 (4H, m), 2.29 (3H, s), 1.85-1.83 (2H, m),1.09-1.04 (6H, m). T158

δ_(H) 8.15 (2H, d), 7.46 (2H, dd), 6.95 (1H, s), 6.94 (1H, s), 4.88 (1H,s with fine splitting), 4.62 (1H, s), 4.62 (1H, s), 3.12-3.10 (1H, m),2.99-2.90 (2H, br. m), 2.40-2.35 (4H, m), 2.31 (3H, s), 2.25- 2.22 (1H,m), 1.93-1.89 (1H, m), 1.08-1.05 (6H, m). T159

δ_(H) 7.31-7.28 (2H, m), 7.13-7.12 (2H, m), 6.94- 6.93 (2H, m),4.84-4.81 (1H, m), 4.57 (1H, d), 3.00-2.99 (4H, m), 2.98-2.85 (2H, br.m), 2.38- 2.33 (4H, m), 2.30 (3H, s), 2.17-2.14 (1H, m), 1.90-1.87 (1H,m), 1.08-1.04 (6H, m). T160

δ_(H) 7.58 (2H, dd), 7.41-7.40 (2H, m), 6.95 (1H, s), 4.87-4.85 (1H, m),4.60 (1H, d), 3.06-3.03 (1H, m), 3.04-2.95 (2H, br. m), 2.40-2.33 (4H,m), 2.30 (3H, s), 2.25-2.20 (1H, m), 1.93-1.88 (1H, m), 1.09-1.05 (6H,m). T161

δ_(H) 8.18 (1H, s), 8.10-8.08 (1H, m), 7.69-7.67 (1H, m), 7.48 (1H, t),6.97 (1H, s), 6.95 (1H, s), 4.91 (1H, d), 4.64 (1H, s), 3.18-3.13 (1H,m), 3.10-2.95 (2H, br. m), 2.40-2.36 (4H, m), 2.31 (3H, s), 1.08 (6H,t). T162

δ_(H) 7.25-7.15 (4H, m), 6.96 (1H, s), 6.94 (1H, s), 4.85 (1H, s), 4.58(1H, br. s), 3.10-3.05 (1H, br. m), 3.00-2.97 (1H, m), 2.87-2.85 (1H,m), 2.47 (3H, s), 2.42-2.34 (4H, m), 2.31 (3H, s), 2.21- 2.17 (1H, m),1.96-1.91 (1H, m), 1.00-1.05 (6H, m). T163

δ_(H) 7.42-7.38 (1H, m), 6.94-6.92 (2H, m), 6.85- 6.83 (1H, m),6.77-6.73 (1H, m), 4.82-4.80 (1H, m), 4.59 (1H, d), 3.38-3.34 (1H, m),3.05-2.91 (2H, br. m), 2.37-2.34 (4H, m), 2.30 (3H, s), 2.19- 2.15(1H,m), 1.85-1.80 (1H, m), 1.08-1.04 (6H, m). T164

δ_(H) 7.22-7.20 (1H, m), 7.05-7.00 (2H, m), 6.94 (1H, s), 6.92 (1H, s),4.83 (1H, s), 4.79 (1H, br. s), 3.85-3.82 (1H, m), 3.06-2.89 (2H, br.m), 2.51 (3H, s), 2.39-2.33 (4H, m), 2.30 (3H, s), 2.18- 2.14 (1H, m),1.99-1.95 (1H, m), 1.05 (6H, t). T165

δ_(H) 7.35 (1H, t), 7.16-7.12 (1H, m), 6.96 (1H, s), 6.61-6.53 (1H, m),4.86 (1H, br. s), 4.66 (1H, s), 3.17-3.09 (2H, m), 2.87-2.85 (1H, m),2.42- 2.35 (4H, m), 2.32 (6H, s), 2.26-2.18 (1H, m), 1.83-1.76 (1H, m),1.08 (6H, t). T166

δ_(H) 7.76-7.74 (3H, m), 6.96 (1H, s), 6.94 (1H, s), 4.89 (1H, br. s),4.62 (1H, s), 3.15-3.13 (1H, m), 3.12-3.07 (1H, br. m), 2.87 (1H, br.s), 2.43- 2.36 (4H, m), 2.30 (3H, s), 2.28-2.25 (1H, m), 1.92-1.90 (1H,m), 1.09-1.06 (6H, m). T167

δ_(H) 8.26-8.24 (1H, m), 8.10 (1H, dd), 7.71 (1H, d), 6.96 (1H, s), 9.95(1H, s), 4.89 (1H, br. s), 4.73 (1H, br. s), 3.62 (1H, br. s), 3.13 (1H,br. s), 2.94 (1H, br. s), 2.39-2.33 (4H, m), 2.31 (3H, s), 1.82-1.80(1H, m), 1.67-1.65 (1H, m), 1.08 (6H, t). T168

δ_(H) 7.58 (1H, s), 7.46 (1H, d), 6.97 (1H, s), 6.95 (1H, s), 4.88 (1H,br. s), 4.64 (1H, s), 3.49-3.47 (1H, m), 3.17-2.86 (2H, br. m),2.40-2.35 (4H, m), 2.32 (3H, s), 1.81-1.79 (1H, m), .158-1.56 (1H, m),1.10-1.06 (6H, m). T169

δ_(H) 7.73 (1H, s), 7.48-7.41 (2H, m), 6.96 (1H, s), 6.93 (1H, s), 4.84(1H, br. s), 4.69 (1H, s), 3.58 (1H, br. s), 3.08-2.93 (2H, br. m),2.38-2.32 (4H, m), 2.31 (3H, s), 2.27-2.35 (1H, m), 1.84- 1.80 (1H, m),1.10-1.05 (6H, m). T170

δ_(H) 7.43-7.38 (1H, m), 7.19-7.14 (1H, m), 7.11- 7.07 (1H, m),7.01-6.96 (1H, m), 6.90-6.89 (2H, m), 4.75 (1H, d), 4.60 (1H, s), 3.35(1H, dd), 2.90- 2.83 (2H, m), 2.37-2.29 (4H, m), 2.28 (3H, s), 2.12-2.07(1H, m), 1.84-1.78 (1H, m), 1.06- 1.01 (6H, m). T171

δ_(H) 7.86 (2H, d), 7.34 (2H, d), 6.91-6.90 (2H, m), 4.76 (1H, d), 4.57(1H, s), 2.97 (1H, dd), 2.87- 2.83 (2H, m), 2.58 (3H, s), 2.42-2.32 (4H,m), 2.28 (3H, s), 2.10-2.02 (1H, m), 1.87-1.82 (1H, m), 1.09-1.05 (6H,m). T172

δ_(H) 7.61 (1H, d), 7.30 (1H, d), 7.12 (1H, dd), 6.94- 6.93 (2H, m),4.81 (1H, d), 4.67 (1H, s), 3.85 (3H, s), 3.40 (1H, dd), 3.04-2.88 (2H,br. s), 2.40- 2.31 (4H, m), 2.30 (3H, s), 2.29-2.26 (1H, m), 1.89-1.86(1H, m), 1.06 (6H, t). T173

δ_(H) 6.89 (1H, s), 6.88 (1H, s), 6.78-6.73 (2H, m), 6.67-6.61 (1H, m),4.66 (1H, d), 4.48 (1H, s), 2.81 (1H, dd), 2.74 (2H, br. s), 2.33-2.27(4H, m), 2.26 (3H, s), 2.05-1.98 (1H, m), 1.77-1.71 (1H, m), 1.02 (6H,t). T174

δ_(H) 7.78-7.73 (2H, m), 7.44-7.42 (1H, m), 7.35 (1H, t), 6.84 (2H, s),4.69 (1H, d), 4.50 (1H, s), 2.93 (1H, dd), 2.79-2.76 (2H, m), 2.54 (3H,s), 2.35-2.26 (4H, m), 2.22 (3H, s), 2.05-2.00 (1H, m), 1.82-1.76 (1H,m), 1.04-0.99 (6H, m). T175

δ_(H) 7.95 (2H, d), 7.28 (2H, d), 6.91-6.90 (2H, m), 4.69 (1H, d), 4.53(1H, s), 4.38 (2H, q), 2.91 (1H, dd), 2.79-2.76 (2H, m), 2.40-2.31 (4H,m), 2.30 (3H, s), 2.03-1.97 (1H, m), 1.83-1.77 (1H, m), 1.43 (2H, t),1.06 (6H, t). T176

δ_(H) 7.94 (2H, d), 7.33 (2H, d), 6.92-6.91 (2H, m), 4.81 (1H, d), 4.60(1H, s), 3.89 (3H, s), 3.02 (1H, dd), 2.97-2.80 (2H, br. m), 2.38-2.30(4H, m), 2.29 (3H, s), 2.16 (1H, dd), 1.93-1.87 (1H, m), 1.07-1.03 (6H,m). T177

δ_(H) 7.78 (1H, dd), 7.71 (1H, dd), 7.59-7.54 (1H, m), 7.37-7.33 (1H,m), 6.91-6.90 (2H, m), 4.79 (1H, d), 4.69 (1H, s), 3.42 (1H, dd), 2.93(1H, br. s), 2.88-2.86 (1H, m), 2.93-2.30 (4H, m), 2.28 (3H, s),2.28-2.26 (1H, m), 1.91-1.85 (1H, m), 1.05 (6H, t). T178

δ_(H) 7.05-6.97 (2H, m), 6.87-6.83 (3H, m), 4.62 (1H, d), 4.41 (1H, s),2.76 (1H, dd), 2.70 (2H, br. s), 2.34-2.24 (5H, m), 2.26 (3H, s),1.97-1.92 (1H, m), 1.71-1.66 (1H, m), 1.00 (6H, t). T179

δ_(H) 7.15 (1H, t), 7.07 (1H, s), 7.02-7.00 (2H, m), 6.89 (1H, s), 6.88(1H, s), 4.70 (1H, d), 4.51 (1H, s), 2.85 (1H, dd), 2.80-2.76 (2H, m),2.37-2.31 (4H, m), 2.32 (3H, s), 2.27 (3H, s), 2.04-1.98 (1H, m),1.87-1.82 (1H, m), 1.05-1.01 (6H, m). T180

δ_(H) 7.11-7.05 (4H, m), 6.88-6.87 (2H, m), 4.67 (1H, d), 4.47 (1H, s),2.84 (1H, dd), 2.77-2.73 (2H, m), 2.36-2.28 (4H, m), 2.30 (3H, s), 2.27(3H, s), 2.01-1.96 (1H, m), 1.84-1.79 (1H, m), 1.05-1.00 (6H, m). T181

δ_(H) 6.90 (1H, s), 6.89 (1H, s), 6.47 (2H, s), 4.70 (1H, d), 4.51 (1H,s), 3.84 (6H, s), 3.80 (3H, s), 2.84-2.79 (3H, m), 2.37-2.30 (4H, m),2.28 (3H, s), 2.07-2.02 (1H, m), 1.86-1.80 (1H, m), 1.07- 1.02 (6H, m).T182

δ_(H) 7.53 (1H, s), 7.49-7.43 (2H, m), 7.38-7.34 (1H, m), 6.89 (1H, s),6.88 (1H, s), 4.71 (1H, d), 4.47 (1H, s), 289 (1H, dd), 2.82-2.78 (2H,m), 2.36-2.26 (4H, m), 2.25 (3H, s), 2.05 (1H, dd), 1.78-1.72 (1H, m),1.02 (6H, t) T183

δ_(H) 7.79 (1H, d), 7.74-7.72 (1H, m), 7.69-7.66 (1H, m), 6.96 (1H, s),6.95 (1H, s), 4.90 (1H, d), 4.60 (1H, s), 3.11 (1H, dd), 2.99 (2H, br.s), 2.40- 2.32 (4H, m), 2.30 (3H, s), 2.29-2.26 (1H, m), 1.90-1.84 (1H,m), 1.09-1.05 (6H, m). T184

δ_(H) 8.29 (1H, d), 7.97 (1H, dd), 7.29 (1H, d), 6.97 (1H, s), 6.95 (1H,s), 4.92 (1H, d), 4.72 (1H, s), 3.26 (1H, dd), 3.03 (2H, br. s), 2.43(3H, s), 2.40- 2.33 (4H, m), 2.32 (3H, s), 2.26 (1H, dd), 1.87- 1.85(1H, m), 1.12-1.06 (6H, m). T185

δ_(H) 7.19-7.16 (2H, m), 6.97-6.90 (4H, m), 4.71 (1H, d), 4.48 (1H, s),2.88 (1H, dd), 2.82-2.78 (2H, m), 2.37-2.30 (4H, m), 2.28 (3H, s), 2.05(1H, dd), 1.83-1.77 (1H, m), 1.05-1.01 (6H, m). T186

d₄-MeOH δ_(H) 6.82 (1H, s), 6.80 (1H, s), 4.87 (1H, d), 4.77 (1H, d),4.63 (1H, d), 2.72 (1H, d), 2.65 (1H, d), 2.23 (3H, s), 2.12 (3H, s),2.08 (3H, s), 2.07-2.03 (1H, m), 1.95-1.86 (1H, m), 1.76- 1.70 (1H, m),1.62-1.55 (1H, m). T187

d₄-MeOH δ_(H) 8.65 (1H, s), 8.54 (1H, br. s), 8.46 (1H, br. s), 6.87(2H, s), 4.82 (1H, d), 4.72 (1H, s), 3.48-3.46 (1H, m), 3.13 (1H, d),3.04 (1H, d), 2.25 (3H, s), 2.25-2.18 (2H, m), 2.09 (3H, s), 2.07 (3H,s), 1.79-1.74 (1H, m), 1.72-1.67 (1H, m). T188

d₄-MeOH δ_(H) 8.93 (1H, s, 8.09-8.06 (2H, m), 7.85-7.78 (2H, m), 6.87(2H, s), 4.90 (1H, s), 4.87 (1H, d), 3.66 (1H, dd), 3.19 (1H, d), 3.09(1H, d), 2.44-2.33 (2H, m), 2.25 (3H, s), 2.09 (3H, s), 2.08 (3H, s).T189

d₄-MeOH δ_(H) 7.23 (2H, s), 4.61 (2H, t), 2.88 (2H, s), 2.09 (6H, s),1.83 (2H, m), 1.69 (2H, m) T190

d₄-MeOH δ_(H) 7.14-7.04 (3H, m), 4.61 (2H, t), 2.88 (2H, s), 2.11 (6H,s), 1.83 (2H, m), 1.69 (2H, m) T191

d₄-MeOH δ_(H) 7.36 (1H, dd), 7.17 (1H, d), 7.15 (1H, d), 2.81 (2H, s),2.48-2.43 (2H, m), 1.84-1.79 (2H, m), 1.69-1.65 (2H, m), 1.51 (6H, s),1.08 (3H, t). T192

d₄-MeOH δ_(H) 6.94 (1H, d), 6.78 (1H, d), 6.73 (1H, dd), 4.59 (2H, s),3.77 (3H, s), 2.82 (2H, s), 2.10 (3H, s), 1.84-1.79 (2H, m), 1.69-1.62(2H, m). T193

d₄-MeOH δ_(H) 7.84 (1H, br. s), 6.78 (2H, s), 4.89 (1H, br. s), 4.84(1H, s), 3.28 (1H, br. s), 3.02 (1H, br. s), 2.94 (1H, br. s), 2.57-2.46(2H, m), 2.53 (3H, s), 2.18 (3H, s), 2.05 (3H, s), 2.03 (3H, s), 2.02(3H, s). T194

d₄-MeOH δ_(H) 8.09-8.06 (1H, m), 8.00-7.98 (1H, m), 7.73-7.70 (2H, m),6.86 (2H, s), 4.99 (1H, s), 4.80 (1H, d), 3.19-3.10 (3H, m), 2.49-2.43(1H, m), 2.34-2.28 (1H, m), 2.25 (3H, s), 2.07 (3H, s), 2.06 (3H, s),1.46 (3H, t). T195

d₄-MeOH δ_(H) 7.04 (1H, br. s), 6.86 (2H, s), 5.93 (1H, br. s), 4.86(1H, br. s), 4.78 (1H, s), 3.18 (1H, br. s), 3.02 (1H, br. s), 2.94 (1H,br. s), 2.59 (3H, s), 2.37 (3H, s), 2.24 (3H, s), 2.16 (3H, s), 2.07(6H, m). T196

d₄-MeOH δ_(H) 8.79 (1H, s), 8.59 (1H, s), 6.87 (1H, s), 4.95 (1H, s),4.92 (1H, d), 3.74-3.71 (1H, m), 2.87 (2H, m), 2.26 (2H, m), 2.18 (3H,s), 2.10 (3H, s), 2.07 (3H, s). T197

d₄-MeOH δ_(H) 7.45-7.42 (3H, m), 7.29-7.23 (2H, m), 7.17-7.15 (2H, m),6.80 (2H, s), 4.82 (1H, br. s), 4.73 (1H, br. s), 3.21 (1H, br. s), 2.90(1H, br. s), 2.84 (1H, br. s), 2.20 (3H s), 2.09-2.07 (2H, m), 2.05 (6H,s). T198

d₄-MeOH δ_(H) 8.78 (1H, br. s), 7.96 (1H, br. s), 6.84 (3H, s), 4.82(2H, br. s), 3.51 (1H, br. s), 2.98 (1H, br. s), 2.90 (1H, br. s), 2.35(1H, br. s), 2.22 (3H, s), 2.04-2.02 (7H, m). T199

d₄-MeOH δ_(H) 7.81 (1H, s), 7.26 (1H, s), 6.92 (1H, s), 6.90 (1H, s),4.91 (1H, d), 4.64 (1H, s), 3.19- 3.17 (1H, m), 2.99-2.95 (2H, m),2.32-2.27 (1H, m), 2.26 (3H, s), 2.09 (3H, s), 2.07 (3H, s), 1.93- 1.90(1H, m). T200

d₄-MeOH δ_(H) 7.95 (1H, br. s), 7.86 (1H, br. s), 7.44 (1H, br. s), 6.88(1H, s), 6.84 (1H, s), 4.86 (1H, br. s), 4.71 (1H, br. s), 3.44-3.40(1H, br. s), 3.07 (1H, br. s), 2.85 (1H, br. s), 2.22 (3H, s), 2.15-2.11 (2H, m), 2.10 (3H, s), 2.05 (3H, s). T201

d₄-MeOH δ_(H) 7.79 (1H, t), 7.53 (2H, d), 6.86 (2H, s), 4.78 (1H, s),4.71 (1H, s), 3.35-3.31 (1H, m), 2.88 (1H, br. s), 2.79 (1H, br. s),2.22 (3H, s), 2.17- 2.09(2H, m), 2.04 (3H, s), 2.02 (3H, s). T202

d₄-MeOH δ_(H) 8.76 (1H, br. s), 8.61 (1H, d), 8.32 (1H, d), 7.96 (1H,d), 7.85 (1H, d), 6.86 (2H, s), 4.84 (1H, s), 4.11 (1H, dd), 3.24 (1H,d), 3.13 (1H, d), 2.58-2.54 (1H, m), 2.24 (3H, s), 2.07 (6H, s),1.95-1.91 (1H, m). T203

d₄-MeOH δ_(H) 9.07 (1H, s), 8.38 (1H, s), 6.87 (2H, s), 4.77 (1H, s),3.77-3.74 (1H, m), 3.04 (2H, br. s), 2.40-2.37 (1H, m), 2.29-2.25 (1H,m), 2.25 (3H, s), 2.06 (3H, s), 2.04 (3H, s). T204

d₄-MeOH δ_(H) 6.85 (2H, s), 6.72 (1H, d), 5.03 (1H, d), 3.96 (1H, s),2.92-2.88 (2H, m), 2.24 (3H, s), 2.06 (3H, s), 2.01 (3H, s). T205

d₆-DMSO δ_(H) 11.92 (1H, s), 7.05 (1H, d), 6.96 (1H, d), 6.77 (1H, s),4.50 (2H, s), 2.74 (2H, br. s), 2.23 (3H, s), 2.03 (3H, s), 1.71-1.65(2H, m), 1.57-1.53 (2H, m). T206

d₆-DMSO δ_(H) 12.21 (1H, s), 7.20 (1H, dd), 6.99 (1H, td), 6.75 (1H,dd), 4.51 (2H, s), 2.76 (2H, br. s), 2.04 (3H, s), 1.71-1.65 (2H, m),1.60-1.52 (2H, m). T207

d₆-DMSO δ_(H) 12.27 (1H, s), 7.21 (2H, s), 6.97 (1H, s), 4.51 (2H, s),2.78 (2H, br. s), 2.05 (3H, s), 1.73-1.63 (2H, m), 1.60-1.51 (2H, m).T208

d₄-MeOH δ_(H) 6.61 (2H, s), 4.64-4.50 (2H, m), 3.74 (3H, s), 2.83 (2H,s), 2.04 (6H, d), 1.87-1.77 (2H, m), 1.70-1.59 (2H, m). T209

d₄-MeOH δ_(H) 8.30 (1H, s), 6.86 (2H, s), 4.89 (1H, s), 4.73 (1H, d),3.47 (1H, dd), 3.09 (1H, d), 3.04 (1H, d), 2.55 (3H, s), 2.39-2.35 (1H,m), 2.30 (3H, s), 2.25 (3H, s), 2.17 (1H, dd), 2.06 (3H, s), 2.04 (3H,s). T210

d₄-MeOH δ_(H) 8.72 (1H, d), 7.72 (1H, s), 7.58 (1H, d), 6.86 (2H, s),4.81 (1H, d), 4.68 (1H, s), 3.51 (1H, dd), 3.10 (1H, d), 3.03 (1H, d),2.33 (1H, dd), 2.25 (3H, s), 2.16-2.11 (1H, m), 2.06 (3H, s), 2.05 (3H,s). T211

d₄-MeOH δ_(H) 7.21-7.19 (1H, m), 6.92-6.90 (2H, m), 6.86 (2H, s), 4.72(1H, d), 4.43 (1H, s), 3.49 (1H, dd), 3.02 (1H, d), 2.93 (1H, d), 2.29(1H, dd), 2.25 (3H, s), 2.05 (6H, s), 1.98-1.93 (1H, m). T212

d₄-MeOH δ_(H) 7.41 (1H, d), 7.29 (1H, dd), 7.19 (1H, d), 4.65-4.60 (2H,m), 2.87 (2H, s), 1.86-1.79 (2H, m), 1.70-1.63 (2H, m). T213

d₄-MeOH δ_(H) 7.44-7.41 (2H, m), 7.08 (2H, t), 6.88 (1H, s), 6.87 (1H,s), 4.89(1H, s), 4.73 (1H, s), 3.68 (1H, d), 3.59 (1H, d), 3.10-3.06(2H, m), 2.25 (3H, s), 2.07 (3H, s), 2.5 (3H, s). T214

d₄-MeOH δ_(H) 8.24 (2H, d), 7.66 (2H, d), 6.88 (2H, s), 4.93 (1H, s),4.68 (1H, s), 3.76 (2H, s), 3.13- 3.11 (2H, m), 2.25 (3H, s), 2.07 (3H,s), 2.05 (3H, s). T215

d₄-MeOH δ_(H) 7.34-7.30 (1H, m), 7.25-7.18 (2H, m), 6.89 (1H, s), 6.87(1H, s), 4.90 (1H, s), 4.75 (1H, s), 3.67 (1H, d), 3.58 (1H, d),3.10-3.05 (2H, m), 2.26 (3H, s), 2.07 (3H, s), 2.05 (3H, s). T216

d₄-MeOH δ_(H) 8.53 (1H, s), 7.83 (1H, d), 7.64 (1H, d), 6.91 (2H, s),3.12 (1H, dd), 2.97 (2H, br. s), 2.47 (1H, dd), 2.27 (3H, s), 1.84-1.79(1H, m), 2.11 (3H, s), 2.08 (3H, s), 1.71 (3H, s), 1.10 (3H, s). T217

d₄-MeOH δ_(H) 7.92 (1H, d), 7.77-7.73 (1H, m), 6.91-6.88(3H, m), 3.04(1H, dd), 2.96-2.92 (2H, m), 2.43(1H, dd), 2.25 (3H, s), 2.11 (3H, s),2.08 (3H, s), 1.76 (1H, dd), 1.70 (3H, s), 1.09 (3H, s). T218

d₄-MeOH δ_(H) 7.41 (1H, d), 6.88 (2H, s), 6.35-6.34 (1H, m), 6.14 (1H,d), 4.72 (1H, d), 4.59 (1H, s), 3.26(1H, dd), 3.02 (1H, d), 2.94 (1H,d), 2.27 (3H, s), 2.18-2.12 (1H, m), 2.08 (3H, s), 2.06 (3H, s),2.05-2.01 (1H, m). T219

d₄-MeOH δ_(H) 7.60 (1H, d), 7.06 (1H, d), 6.89 (2H, s), 4.79 (1H, d),4.47 (1H, s), 3.63 (1H, dd), 3.06 (1H, d), 3.00 (1H, d), 2.36 (1H, dd),2.27 (3H, s), 2.07 (6H, s), 1.97-1.91 (1H, m). T220

δ_(H) 7.39 (1H, dd), 7.27-7.33 (1H, m), 6.97 (1H, dd), 4.68 (2H, m),2.74 (2H, br. s), 2.48 (2H, q), 1.78- 1.87 (2H, m), 1.56 (2H, m), 1.11(3H, t). T221

δ_(H) 7.05-6.99 (1H, m), 4.76-4.67 (2H, m), 2.84 (2H, br. s), 2.38 (3H,s), 2.24 (3H, d), 2.05 (3H, d), 1.88-1.85 (2H, m), 1.64-1.58 (2H, m).T222

d₄-MeOH δ_(H) 8.11 (2H, dd), 8.61 (2H, t), 6.86 (2H, s), 4.81 (1H, s),4.67 (1H, d), 3.81 (1H, dd), 3.14 (1H, d), 3.03 (1H, d), 2.24 (3H, s),2.23-2.19 (1H, m), 2.11-2.09 (1H, m), 2.06 (3H, s), 2.02 (3H, s). T223

d₄-MeOH δ_(H) 7.39-7.36 (2H, m), 6.98-6.94 (2H, m), 6.88 (1H, s), 6.86(1H, s), 4.95 (1H, s), 4.53 (1H, s), 3.63 (1H, d), 3.08 (1H, d), 3.03(1H, d), 2.88-2.86 (1H, m), 2.25 (3H, s), 2.09 (3H, s), 2.06 (3H, s).T224

d₄-MeOH δ_(H) 7.81-7.76 (1H, m), 7.73-7.70 (1H, m), 7.29-7.23 (1H, m),6.88 (2H, s), 4.96 (1H, s), 4.79 (1H, d), 3.47 (1H, dd), 3.04-2.92 (2H,m), 2.25 (3H, s), 2.11-2.07(1H, m), 2.07 (3H, s), 2.04 (3H, s),1.96-1.88 (1H, m). T225

d₄-MeOH δ_(H) 7.16-7.12 (1H, m), 7.01-6.90 (2H, m), 6.78 (1H, s), 6.76(1H, s), 4.94 (1H, s), 4.54 (1H, s), 3.39 (1H, d), 3.12 (1H, d),2.28-2.80 (2H, br. m), 2.14 (3H, s), 2.00 (3H, s), 1.96 (3H, s). T226

d₄-MeOH δ_(H) 7.43 (1H, s), 7.38 (1H, s), 6.88 (2H, s), 6.42 (1H, d),4.93 (1H, s), 4.71 (1H, d), 3.09 (1H, dd), 2.99 (1H, d), 2.93 (1H, d),2.27 (3H, s), 2.17 (1H, dd), 2.08 (6H, m), 1.85-1.80 (1H, m). T227

δ_(H) 7.92-7.81 (3H, m), 7.42-7.29 (2H, m), 6.85 (2H, s), 4.78 (1H, d),4.59 (1H, s), 3.57 (1H, dd), 3.14 (1H, d), 3.00 (1H, d), 2.31 (1H, dd),2.24 (3H, s), 2.07 (3H, s), 2.05 (3H, s), 2.04-1.98 (1H, m). T228

δ_(H) 6.86 (2H, s), 6.47 (2H, s), 5.01 (2H, s), 2.74 (2H, s), 2.23 (3H,s), 2.08 (3H, s), 2.06 (3H, s). T229

δ_(H) 6.65 (2H, s), 6.26 (1H, s), 4.75 (1H, s), 4.67 (1H, s), 2.62 (1H,d), 2.52 (1H, d), 2.03 (3H, s), 1.84 (3H, s), 1.80 (3H, s), 0.00 (9H,s).

The compounds of the following Tables 1 to 146 can be obtained in ananalogous manner.

Table 1 covers compounds of formula (A)

wherein R¹, R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

TABLE 1 R⁶ R⁷ R⁸ R⁹ R¹⁰ R¹¹ 1.001 H H H H H H 1.002 H H H H H CH₃ 1.003H H H H H CH₂OH 1.004 H H H H H CH₂OCH₃ 1.005 H H H H H CH₂OCH₂CH₃ 1.006H H H H H CH₂OCH₂OCH₃ 1.007 H H H H H CH₂OCH₂OCH₂CH₃ 1.007 H H H H HCH₂OCH₂CO₂CH₃ 1.008 H H H H H CH₂OCH₂CO₂CH₂CH₃ 1.009 H H H H H CH₂OCH₂CN1.010 H H H H H CH(OH)CH₃ 1.011 H H H H H CH(CH₃)OCH₃ 1.012 H H H H HCH(CH₃)OCH₂CH₃ 1.013 H H H H H CHO 1.014 H H H H H COCH₃ 1.015 H H H H HCH₂COCH₃ 1.016 H H H H H CH₂CH₂COCH₃ 1.017 H H H H H CO₂H 1.018 H H H HH CO₂CH₃ 1.019 H H H H H CO₂CH₂CH₃ 1.020 H H H H H CH₂CO₂CH₃ 1.021 H H HH H CH₂CO₂CH₂CH₃ 1.022 H H H H H CH₂CH₂CO₂CH₃ 1.023 H H H H HCH₂CH₂CO₂CH₂CH₃ 1.024 H H H H H CONH₂ 1.025 H H H H H CONHCH₃ 1.026 H HH H H CONHCH₂CH₃ 1.027 H H H H H CON(CH₃)₂ 1.030 H H H H H CON(CH₂CH₃)₂1.031 H H H H H CON(CH₃)OCH₃ 1.032 H H H H H CH═NOH 1.033 H H H H HCH═NOCH₃ 1.034 H H H H H CH═NOCH₂CH₃ 1.035 H H H H H C(CH₃)═NOH 1.036 HH H H H C(CH₃)═NOCH₃ 1.037 H H H H H CH₂OC(O)CH₃ 1.038 H H H H HCH₂OC(O)CH₂CH₃ 1.039 H H H H H CH₂OC(O)CH(CH₃)₂ 1.040 H H H H HCH₂OC(O)C(CH₃)₃ 1.039 H H H H H CH₂OC(O)NHCH₃ 1.040 H H H H HCH₂OC(O)NHCH₂CH₃ 1.041 H H H H H CH₂OC(O)NHCH₂CH₂CH₃ 1.042 H H H H HCH₂OC(O)NHC(CH₃)₃ 1.043 H H H H H CH₂NH₂ 1.044 H H H H H CH₂NHCHO 1.045H H H H H CH₂NHC(O)CH₃ 1.046 H H H H H CH₂NHC(O)OCH₃ 1.047 H H H H HNHCO₂CH₃ 1.048 H H H H H NHCO₂C(CH₃)₃ 1.049 H H H H H CN 1.050 H H H H HCH₂SCH₃ 1.051 H H H H H CH₂SCH₂CH₃ 1.052 H H H H H CH₂SCH₂CH₂CH₃ 1.053 HH H H H CH₂SCH(CH₃)₂ 1.054 H H H H H CH₂S(O)CH₃ 1.055 H H H H HCH₂SO₂CH₃ 1.056 H H H H H CH₂SCH₂CH₃ 1.057 H H H H H CH₂S(O)CH₂CH₃ 1.058H H H H H CH₂SO₂CH₂CH₃ 1.059 H H H H H OCH₃ 1.060 H H H H H OCH₂CH₃1.061 H H H H H CH(OCH₃)₂ 1.062 H H H H H CH(OCH₂CH₃)₂ 1.063 H H H H H1,3-dioxolan-2-yl 1.064 11 H H H H 1,3-dioxan-2-yl 1.065 H H H H H5,5-dimethyl-1,3-dioxan- 2-yl 1.066 H H H H H CH₂CH₃ 1.067 H H H H Hn-propyl 1.068 H H H H H isopropyl 1.069 H H H H H n-butyl 1.070 H H H HH isobutyl 1.071 H H H H H sec-butyl 1.072 H H H H H tert-butyl 1.073 HH H H H n-pentyl 1.074 H H H H H neopentyl 1.075 H H H H H n-hexyl 1.076H H H H H n-heptyl 1.077 H H H H H CH₂CN 1.078 H H H H H cyclopropyl1.079 H H H H H cyclobutyl 1.080 H H H H H cyclopentyl 1.081 H H H H Hcyclohexyl 1.082 H H H H H CH₂-cyclopropyl 1.083 H H H H H benzyl 1.084H H H H H CH₂CF₃ 1.085 H H H H H CH₂F 1.086 H H H H H CHF₂ 1.087 H H H HH CF₃ 1.088 H H H H CH₃ H 1.089 H H H H CH₂CH₃ H 1.090 H H H H n-propylH 1.091 H H H H isopropyl H 1.092 H H H H n-butyl H 1.093 H H H Hisobutyl H 1.094 H H H H sec-butyl H 1.095 H H H H tert-butyl H 1.096 HH H H vinyl H 1.097 H H H H ethynyl H 1.098 H H H Htrimethylsilylethynyl H 1.099 H H H H CH₂OH H 1.100 H H H H CH₂OCH₃ H1.101 H H H H CH₂OCH₂CH₃ H 1.102 H H H H CH₂OCH₂OCH₃ H 1.103 H H H HCH₂OCH₂OCH₂CH₃ H 1.104 H H 11 H CH₂OCH₂CH₂OCH₃ H 1.105 H H H H CHO H1.106 H H H H COCH₃ H 1.107 H H H H CO₂H H 1.108 H H H H CO₂CH₃ H 1.109H H H H CO₂CH₂CH₃ H 1.110 H H H H CONH₂ H 1.111 H H H H CONHCH₃ H 1.112H H H H CONHCH₂CH₃ H 1.113 H H H H CON(CH₃)₂ H 1.114 H H H HCON(CH₂—CH₃)₂ H 1.115 H H H H CON(CH₃)OCH₃ H 1.116 H H H H CH═NOH H1.117 H H H H CH═N—OCH₃ H 1.118 H H H H CH═N—OCH₂CH₃ H 1.119 H H H HC(CH₃)═N—OH H 1.120 H H H H C(CH₃)═N—OCH₃ H 1.121 H H H H CH₂OC(O)—NHCH₃H 1.122 H H H H CH₂NH₂ H 1.123 H H H H CH₂NHCHO H 1.124 H H H HCH₂NHC(O)CH₃ H 1.125 H H H H CH₂NHC(O)OCH₃ H 1.126 H H H H NHCO₂CH₃ H1.127 H H H H NHCO₂C(CH₃)₃ H 1.128 H H H H CH(OH)CH₃ H 1.129 H H H HCH(CH₃)OCH₃ H 1.130 H H H H CN H 1.131 H H H H CH₂SCH₃ H 1.132 H H H HCH₂S(O)CH₃ H 1.133 H H H H CH₂SO₂CH₃ H 1.134 H H H H CH₂SCH₂CH₃ H 1.135H H H H CH₂S(O)CH₂CH₃ H 1.136 H H H H CH₂SO₂CH₂CH₃ H 1.137 H H H H OCH₃H 1.138 H H H H OCH₂CH₃ H 1.139 H H H H CH(OCH₃)₂ H 1.140 H H H HCH(OCH₂CH₃)₂ H 1.141 H H H H cyclopropyl H 1.142 H H H H cyclobutyl H1.143 H H H H cyclopentyl H 1.144 H H H H cyclohexyl H 1.145 H H H H F H1.146 H H H H Cl H 1.147 H H H H Br H 1.148 H H H H I H 1.149 H H H H OHH 1.150 H H H H phenyl H 1.151 H H H H 2-acetylphenyl H 1.152 H H H H3-acetylphenyl H 1.153 H H H H 4-acetylphenyl H 1.154 H H H H2-chlorophenyl H 1.155 H H H H 3-chlorophenyl H 1.156 H H H H4-chlorophenyl H 1.157 H H H H 2-cyanophenyl H 1.158 H H H H3-cyanophenyl H 1.159 H H H H 4-cyanophenyl H 1.160 H H H H2-fluorophenyl H 1.161 H H H H 3-fluorophenyl H 1.162 H H H H4-fluorophenyl H 1.163 H H H H 2-methoxyphenyl H 1.164 H H H H3-methoxyphenyl H 1.165 H H H H 4-methoxyphenyl H 1.166 H H H H2-methylphenyl H 1.167 H H H H 3-methylphenyl H 1.168 H H H H4-methylphenyl H 1.169 H H H H 2-nitrophenyl H 1.170 H H H H3-nitrophenyl H 1.171 H H H H 4-nitrophenyl H 1.172 H H H H2-thiomethylphenyl H 1.173 H H H H 3-thiomethylphenyl H 1.174 H H H H4-thiomethylphenyl H 1.175 H H H H 2-trifluoromethoxyphenyl H 1.176 H HH H 3-trifluoromethoxyphenyl H 1.177 H H H H 4-trifluoromethoxyphenyl H1.178 H H H H 2-trifluoromethylphenyl H 1.179 H H H H3-trifluoromethylphenyl H 1.180 H H H H 4-trifluoromethylphenyl H 1.181H H H H 2,3-dichlorophenyl H 1.182 H H H H 2,4-dichlorophenyl H 1.183 HH H H 2,5-dichlorophenyl H 1.184 H H H H 2,6-dichlorophenyl H 1.185 H HH H 3,4-dichlorophenyl H 1.186 H H H H 3,5-dichlorophenyl H 1.187 H H HH 2,3-difluorophenyl H 1.188 H H H H 2,4-difluorophenyl H 1.189 H H H H2,5-difluorophenyl H 1.190 H H H H 2,6-difluorophenyl H 1.191 H H H H3,4-difluorophenyl H 1.192 H H H H 3,5-difluorophenyl H 1.193 H H H H2,4,6-trifluorophenyl H 1.194 H H H H 2,4-dimethylphenyl H 1.195 H H H H2,4,6-trimethylphenyl H 1.196 H H H H 3,4,5-trimethoxyphenyl h 1.197 H HH H 2-chloro-3-cyanophenyl H 1.198 H H H H 2-chloro-4-cyanophenyl H1.199 H H H H 2-chloro-5-cyanophenyl H 1.200 H H H H2-chloro-6-cyanophenyl H 1.201 H H H H 3-chloro-2-cyanophenyl H 1.202 HH H H 3-chloro-4-cyanophenyl H 1.203 H H H H 3-chloro-5-cyanophenyl H1.204 H H H H 5-chloro-2-cyanophenyl H 1.205 H H H H4-chloro-2-cyanophenyl H 1.206 H H H H 4-chloro-3-cyanophenyl H 1.207 HH H H 2-chloro-3-fluorophenyl H 1.208 H H H H 2-chloro-4-fluorophenyl H1.209 H H H H 2-chloro-5-fluorophenyl H 1.210 H H H H2-chloro-6-fluorophenyl H 1.211 H H H H 3-chloro-2-fluorophenyl H 1.212H H H H 3-chloro-4-fluorophenyl H 1.213 H H H H 3-chloro-5-fluorophenylH 1.214 H H H H 5-chloro-2-fluorophenyl H 1.215 H H H H4-chloro-2-fluorophenyl H 1.216 H H H H 4-chloro-3-fluorophenyl H 1.217H H H H 2-chloro-3-methylphenyl H 1.218 H H H H 2-chloro-4-methylphenylH 1.219 H H H H 2-chloro-5-methylphenyl H 1.220 H H H H2-chloro-6-methylphenyl H 1.221 H H H H 3-chloro-2-methylphenyl H 1.222H H H H 3-chloro-4-methylphenyl H 1.223 H H H H 3-chloro-5-methylphenylH 1.224 H H H H 5-chloro-2-methylphenyl H 1.225 H H H H4-chloro-2-methylphenyl H 1.226 H H H H 4-chloro-3-methylphenyl H 1.227H H H H 2-cyano-3-fluorophenyl H 1.228 H H H H 2-cyano-4-fluorophenyl H1.229 H H H H 2-cyano-5-fluorophenyl H 1.230 H H H H2-cyano-6-fluorophenyl H 1.231 H H H H 3-cyano-2-fluorophenyl H 1.232 HH H H 3-cyano-4-fluorophenyl H 1.233 H H H H 3-cyano-5-fluorophenyl H1.234 H H H H 5-cyano-2-fluorophenyl H 1.235 H H H H4-cyano-2-fluorophenyl H 1.236 H H H H 4-cyano-3-fluorophenyl H 1.237 HH H H 2-fluoro-3-methylphenyl H 1.238 H H H H 2-fluoro-4-methylphenyl H1.239 H H H H 2-fluoro-5-methylphenyl H 1.240 H H H H2-fluoro-6-methylphenyl H 1.241 H H H H 3-fluoro-2-methylphenyl H 1.242H H H H 3-fluoro-4-methylphenyl H 1.243 H H H H 3-fluoro-5-methylphenylH 1.244 H H H H 5-fluoro-2-methylphenyl H 1.245 H H H H4-fluoro-2-methylphenyl H 1.246 H H H H 4-fluoro-3-methylphenyl H 1.247H H H H pyridin-2-yl H 1.248 H H H H pyridin-3-yl H 1.249 H H H Hpyridin-4-yl H 1.250 H H H H 3-chloropyridin-2-yl H 1.251 H H H H4-chloropyridin-2-yl H 1.252 H H H H 5-chloropyridin-2-yl H 1.253 H H HH 6-chloropyridin-2-yl H 1.254 H H H H 2-chloropyridin-3-yl H 1.255 H HH H 4-chloropyridin-3-yl H 1.256 H H H H 5-chloropyridin-3-yl H 1.257 HH H H 2-chloropyridin-4-yl H 1.258 H H H H 3-chloropyridin-4-yl H 1.259H H H H 2-chloropyridin-5-yl H 1.260 H H H H 3-cyanopyridin-2-yl H 1.261H H H H 4-cyanopyridin-2-yl H 1.262 H H H H 5-cyanopyridin-2-yl H 1.263H H H H 6-cyanopyridin-2-yl H 1.264 H H H H 2-cyanopyridin-3-yl H 1.265H H H H 4-cyanopyridin-3-yl H 1.266 H H H H 5-cyanopyridin-3-yl H 1.267H H H H 2-cyanopyridin-5-yl H 1.268 H H H H 3-fluoropyridin-2-yl H 1.269H H H H 4-fluoropyridin-2-yl H 1.270 H H H H 5-fluoropyridin-2-yl H1.271 H H H H 6-fluoropyridin-2-yl H 1.272 H H H H 2-fluoropyridin-3-ylH 1.273 H H H H 4-fluoropyridin-3-yl H 1.274 H H H H5-fluoropyridin-3-yl H 1.275 H H H H 2-fluoropyridin-5-yl H 1.276 H H HH 3-nitropyridin-2-yl H 1.277 H H H H 4-nitropyridin-2-yl H 1.278 H H HH 5-nitropyridin-2-yl H 1.279 H H H H 6-nitropyridin-2-yl H 1.280 H H HH 2-nitropyridin-3-yl H 1.281 H H H H 4-nitropyridin-3-yl H 1.282 H H HH 5-nitropyridin-3-yl H 1.283 H H H H 2-nitropyridin-5-yl H 1.284 H H HH 3-trifluoromethylpyridin-2-yl H 1.285 H H H H4-trifluoromethylpyridin-2-yl H 1.286 H H H H5-trifluoromethylpyridin-2-yl H 1.287 H H H H6-trifluoromethylpyridin-2-yl H 1.288 H H H H2-trifluoromethylpyridin-3-yl H 1.289 H H H H4-trifluoromethylpyridin-3-yl H 1.290 H H H H5-trifluoromethylpyridin-3-yl H 1.291 H H H H2-trifluoromethylpyridin-5-yl H 1.292 H H H H 2,6-bis(trifluoromethyl)-H pyridin-3-yl 1.293 H H H H 2,6-bis(trifluoromethyl)- H pyridin-4-yl1.294 H H H H 3,5-bis(trifluoromethyl)- H pyridin-2-yl 1.295 H H H H2-thienyl H 1.296 H H H H 3-thienyl H 1.297 H H H H 5-cyanothien-2-yl H1.298 H H H H 2-furyl H 1.299 H H H H 3-furyl H 1.300 H H H H1-methyl-1,2,3-triazol-4-yl H 1.301 H H H H 2-methylthiopyrimidin-4-yl H1.302 H H H H 5-methyl-2-methyl- H thiopyrimidin-4-yl 1.303 H H H Hpyrazin-2-yl H 1.304 H H H H 3,6-dimethylpyrazin-2-yl H 1.305 H H H H3-cyanopyrazin-2-yl H 1.306 H H H H quinolin-2-yl H 1.307 H H H H3-ethylquinolin-2-yl H 1.308 H H H H benzyl H 1.309 H H H H4-fluorobenzyl H 1.310 H H H H 4-chlorobenzyl H 1.311 H H H H4-methylbenzyl H 1.312 H H H H 2,4-dimethylbenzyl H 1.313 H H H H2,4,6-trimethylbenzyl H 1.314 H H H H CH₃ CH₃ 1.315 H H H H CH₂CH₃ CH₃1.316 H H H H n-propyl CH₃ 1.317 H H H H isopropyl CH₃ 1.318 H H H Hn-butyl CH₃ 1.319 H H H H isobutyl CH₃ 1.320 H H H H sec-butyl CH₃ 1.321H H H H tert-butyl CH₃ 1.322 H H H H vinyl CH₃ 1.323 H H H H ethynyl CH₃1.324 H H H H trimethylsilylethynyl CH₃ 1.325 H H H H CH₂OH CH₃ 1.326 HH H H CH₂OCH₃ CH₃ 1.327 H H H H CH₂OCH₂CH₃ CH₃ 1.328 H H H H CH₂OCH₂OCH₃CH₃ 1.329 H H H H CH₂OCH₂OCH₂CH₃ CH₃ 1.330 H H H H CH₂OCH₂CH₂OCH₃ CH₃1.331 H H H H CHO CH₃ 1.332 H H H H COCH₃ CH₃ 1.333 H H H H CO₂H CH₃1.337 H H H H CO₂CH₃ CH₃ 1.335 H H H H CO₂CH₂CH₃ CH₃ 1.336 H H H H CONH₂CH₃ 1.337 H H H H CONHCH₃ CH₃ 1.338 H H H H CONHCH₂CH₃ CH₃ 1.339 H H H HCON(CH₃)₂ CH₃ 1.340 H H H H CON(CH₂—CH₃)₂ CH₃ 1.341 H H H H CON(CH₃)OCH₃CH₃ 1.342 H H H H CH═NOH CH₃ 1.343 H H H H CH═N—OCH₃ CH₃ 1.344 H H H HCH═N—OCH₂CH₃ CH₃ 1.345 H H H H C(CH₃)═N—OH CH₃ 1.346 H H H HC(CH₃)═N—OCH₃ CH₃ 1.347 H H H H CH₂OC(O)—NHCH₃ CH₃ 1.348 H H H H CH₂NH₂CH₃ 1.349 H H H H CH₂NHCHO CH₃ 1.350 H H H H CH₂NHC(O)CH₃ CH₃ 1.351 H HH H CH₂NHC(O)OCH₃ CH₃ 1.352 H H H H NHCO₂CH₃ CH₃ 1.353 H H H HNHCO₂C(CH₃)₃ CH₃ 1.354 H H H H CH(OH)CH₃ CH₃ 1.355 H H H H CH(CH₃)OCH₃CH₃ 1.356 H H H H CN CH₃ 1.357 H H H H CH₂SCH₃ CH₃ 1.358 H H H HCH₂S(O)CH₃ CH₃ 1.359 H H H H CH₂SO₂CH₃ CH₃ 1.360 H H H H CH₂SCH₂CH₃ CH₃1.361 H H H H CH₂S(O)CH₂CH₃ CH₃ 1.362 H H H H CH₂SO₂CH₂CH₃ CH₃ 1.363 H HH H OCH₃ CH₃ 1.364 H H H H OCH₂CH₃ CH₃ 1.365 H H H H CH(OCH₃)₂ CH₃ 1.366H H H H CH(OCH₂CH₃)₂ CH₃ 1.367 H H H H cyclopropyl CH₃ 1.368 H H H Hcyclobutyl CH₃ 1.369 H H H H cyclopentyl CH₃ 1.370 H H H H cyclohexylCH₃ 1.371 H H H H F CH₃ 1.372 H H H H Cl CH₃ 1.373 H H H H Br CH₃ 1.374H H H H I CH₃ 1.375 H H H H OH CH₃ 1.376 H H H H phenyl CH₃ 1.377 H H HH 2-acetylphenyl CH₃ 1.378 H H H H 3-acetylphenyl CH₃ 1.379 H H H H4-acetylphenyl CH₃ 1.380 H H H H 2-chlorophenyl CH₃ 1.381 H H H H3-chlorophenyl CH₃ 1.382 H H H H 4-chlorophenyl CH₃ 1.383 H H H H2-cyanophenyl CH₃ 1.384 H H H H 3-cyanophenyl CH₃ 1.385 H H H H4-cyanophenyl CH₃ 1.386 H H H H 2-fluorophenyl CH₃ 1.387 H H H H3-fluorophenyl CH₃ 1.388 H H H H 4-fluorophenyl CH₃ 1.389 H H H H2-methoxyphenyl CH₃ 1.390 H H H H 3-methoxyphenyl CH₃ 1.391 H H H H4-methoxyphenyl CH₃ 1.392 H H H H 2-methylphenyl CH₃ 1.393 H H H H3-methylphenyl CH₃ 1.394 H H H H 4-methylphenyl CH₃ 1.395 H H H H2-nitrophenyl CH₃ 1.396 H H H H 3-nitrophenyl CH₃ 1.397 H H H H4-nitrophenyl CH₃ 1.398 H H H H 2-thiomethylphenyl CH₃ 1.399 H H H H3-thiomethylphenyl CH₃ 1.400 H H H H 4-thiomethylphenyl CH₃ 1.401 H H HH 2-trifluoromethoxyphenyl CH₃ 1.402 H H H H 3-trifluoromethoxyphenylCH₃ 1.403 H H H H 4-trifluoromethoxyphenyl CH₃ 1.404 H H H H2-trifluoromethylphenyl CH₃ 1.405 H H H H 3-trifluoromethylphenyl CH₃1.406 H H H H 4-trifluoromethylphenyl CH₃ 1.407 H H H H2,3-dichlorophenyl CH₃ 1.408 H H H H 2,4-dichlorophenyl CH₃ 1.409 H H HH 2,5-dichlorophenyl CH₃ 1.410 H H H H 2,6-dichlorophenyl CH₃ 1.411 H HH H 3,4-dichlorophenyl CH₃ 1.412 H H H H 3,5-dichlorophenyl CH₃ 1.413 HH H H 2,3-difluorophenyl CH₃ 1.414 H H H H 2,4-difluorophenyl CH₃ 1.415H H H H 2,5-difluorophenyl CH₃ 1.416 H H H H 2,6-difluorophenyl CH₃1.417 H H H H 3,4-difluorophenyl CH₃ 1.418 H H H H 3,5-difluorophenylCH₃ 1.419 H H H H 2,4,6-trifluorophenyl CH₃ 1.420 H H H H2,4-dimethylphenyl CH₃ 1.421 H H H H 2,4,6-trimethylphenyl CH₃ 1.422 H HH H 3,4,5-trimethoxyphenyl CH₃ 1.423 H H H H 2-chloro-3-cyanophenyl CH₃1.424 H H H H 2-chloro-4-cyanophenyl CH₃ 1.425 H H H H2-chloro-5-cyanophenyl CH₃ 1.426 H H H H 2-chloro-6-cyanophenyl CH₃1.427 H H H H 3-chloro-2-cyanophenyl CH₃ 1.428 H H H H3-chloro-4-cyanophenyl CH₃ 1.429 H H H H 3-chloro-5-cyanophenyl CH₃1.430 H H H H 5-chloro-2-cyanophenyl CH₃ 1.431 H H H H4-chloro-2-cyanophenyl CH₃ 1.432 H H H H 4-chloro-3-cyanophenyl CH₃1.433 H H H H 2-chloro-3-fluorophenyl CH₃ 1.434 H H H H2-chloro-4-fluorophenyl CH₃ 1.435 H H H H 2-chloro-5-fluorophenyl CH₃1.436 H H H H 2-chloro-6-fluorophenyl CH₃ 1.437 H H H H3-chloro-2-fluorophenyl CH₃ 1.438 H H H H 3-chloro-4-fluorophenyl CH₃1.439 H H H H 3-chloro-5-fluorophenyl CH₃ 1.440 H H H H5-chloro-2-fluorophenyl CH₃ 1.441 H H H H 4-chloro-2-fluorophenyl CH₃1.442 H H H H 4-chloro-3-fluorophenyl CH₃ 1.443 H H H H2-chloro-3-methylphenyl CH₃ 1.444 H H H H 2-chloro-4-methylphenyl CH₃1.445 H H H H 2-chloro-5-methylphenyl CH₃ 1.446 H H H H2-chloro-6-methylphenyl CH₃ 1.447 H H H H 3-chloro-2-methylphenyl CH₃1.448 H H H H 3-chloro-4-methylphenyl CH₃ 1.449 H H H H3-chloro-5-methylphenyl CH₃ 1.450 H H H H 5-chloro-2-methylphenyl CH₃1.451 H H H H 4-chloro-2-methylphenyl CH₃ 1.452 H H H H4-chloro-3-methylphenyl CH₃ 1.453 H H H H 2-cyano-3-fluorophenyl CH₃1.454 H H H H 2-cyano-4-fluorophenyl CH₃ 1.455 H H H H2-cyano-5-fluorophenyl CH₃ 1.456 H H H H 2-cyano-6-fluorophenyl CH₃1.457 H H H H 3-cyano-2-fluorophenyl CH₃ 1.458 H H H H3-cyano-4-fluorophenyl CH₃ 1.459 H H H H 3-cyano-5-fluorophenyl CH₃1.460 H H H H 5-cyano-2-fluorophenyl CH₃ 1.461 H H H H4-cyano-2-fluorophenyl CH₃ 1.462 H H H H 4-cyano-3-fluorophenyl CH₃1.463 H H H H 2-fluoro-3-methylphenyl CH₃ 1.464 H H H H2-fluoro-4-methylphenyl CH₃ 1.465 H H H H 2-fluoro-5-methylphenyl CH₃1.466 H H H H 2-fluoro-6-methylphenyl CH₃ 1.467 H H H H3-fluoro-2-methylphenyl CH₃ 1.468 H H H H 3-fluoro-4-methylphenyl CH₃1.469 H H H H 3-fluoro-5-methylphenyl CH₃ 1.470 H H H H5-fluoro-2-methylphenyl CH₃ 1.471 H H H H 4-fluoro-2-methylphenyl CH₃1.472 H H H H 4-fluoro-3-methylphenyl CH₃ 1.473 H H H H pyridin-2-yl CH₃1.474 H H H H pyridin-3-yl CH₃ 1.475 H H H H pyridin-4-yl CH₃ 1.476 H HH H 3-chloropyridin-2-yl CH₃ 1.477 H H H H 4-chloropyridin-2-yl CH₃1.478 H H H H 5-chloropyridin-2-yl CH₃ 1.479 H H H H6-chloropyridin-2-yl CH₃ 1.480 H H H H 2-chloropyridin-3-yl CH₃ 1.481 HH H H 4-chloropyridin-3-yl CH₃ 1.482 H H H H 5-chloropyridin-3-yl CH₃1.483 H H H H 2-chloropyridin-4-yl CH₃ 1.484 H H H H3-chloropyridin-4-yl CH₃ 1.485 H H H H 2-chloropyridin-5-yl CH₃ 1.486 HH H H 3-cyanopyridin-2-yl CH₃ 1.487 H H H H 4-cyanopyridin-2-yl CH₃1.488 H H H H 5-cyanopyridin-2-yl CH₃ 1.489 H H H H 6-cyanopyridin-2-ylCH₃ 1.490 H H H H 2-cyanopyridin-3-yl CH₃ 1.491 H H H H4-cyanopyridin-3-yl CH₃ 1.492 H H H H 5-cyanopyridin-3-yl CH₃ 1.493 H HH H 2-cyanopyridin-5-yl CH₃ 1.494 H H H H 3-fluoropyridin-2-yl CH₃ 1.495H H H H 4-fluoropyridin-2-yl CH₃ 1.496 H H H H 5-fluoropyridin-2-yl CH₃1.497 H H H H 6-fluoropyridin-2-yl CH₃ 1.498 H H H H2-fluoropyridin-3-yl CH₃ 1.499 H H H H 4-fluoropyridin-3-yl CH₃ 1.500 HH H H 5-fluoropyridin-3-yl CH₃ 1.501 H H H H 2-fluoropyridin-5-yl CH₃1.502 H H H H 3-nitropyridin-2-yl CH₃ 1.503 H H H H 4-nitropyridin-2-ylCH₃ 1.504 H H H H 5-nitropyridin-2-yl CH₃ 1.505 H H H H6-nitropyridin-2-yl CH₃ 1.506 H H H H 2-nitropyridin-3-yl CH₃ 1.507 H HH H 4-nitropyridin-3-yl CH₃ 1.508 H H H H 5-nitropyridin-3-yl CH₃ 1.509H H H H 2-nitropyridin-5-yl CH₃ 1.510 H H H H3-trifluoromethylpyridin-2-yl CH₃ 1.511 H H H H4-trifluoromethylpyridin-2-yl CH₃ 1.512 H H H H5-trifluoromethylpyridin-2-yl CH₃ 1.513 H H H H6-trifluoromethylpyridin-2-yl CH₃ 1.514 H H H H2-trifluoromethylpyridin-3-yl CH₃ 1.515 H H H H4-trifluoromethylpyridin-3-yl CH₃ 1.516 H H H H5-trifluoromethylpyridin-3-yl CH₃ 1.517 H H H H2-trifluoromethylpyridin-5-yl CH₃ 1.518 H H H H 2,6-bis(trifluoromethyl)CH₃ pyridin-3-yl 1.519 H H H H 2,6-bis(trifluoromethyl) CH₃ pyridin-4-yl1.520 H H H H 3,5-bis(trifluoromethyl)- CH₃ pyridin-2-yl 1.521 H H H H2-thienyl CH₃ 1.522 H H H H 3-thienyl CH₃ 1.523 H H H H5-cyanothien-2-yl CH₃ 1.524 H H H H 2-furyl CH₃ 1.525 H H H H 3-furylCH₃ 1.526 H H H H 1-methyl-1,2,3-triazol-4-yl CH₃ 1.527 H H H H2-methylthiopyrimidin-4-yl CH₃ 1.528 H H H H 5-methyl-2-methyl- CH₃thiopyrimidin-4-yl 1.529 H H H H pyrazin-2-yl CH₃ 1.530 H H H H3,6-dimethylpyrazin-2-yl CH₃ 1.531 H H H H 3-cyanopyrazin-2-yl CH₃ 1.532H H H H quinolin-2-yl CH₃ 1.533 H H H H 3-ethylquinolin-2-yl CH₃ 1.534 HH H H benzyl CH₃ 1.535 H H H H 4-fluorobenzyl CH₃ 1.536 H H H H4-chlorobenzyl CH₃ 1.537 H H H H 4-methylbenzyl CH₃ 1.538 H H H H2,4-dimethylbenzyl CH₃ 1.539 H H H H 2,4,6-trimethylbenzyl CH₃ 1.540 CH₃H H H CH₃ H 1.541 CH₃ H H H CH₂CH₃ H 1.542 CH₃ H H H n-propyl H 1.543CH₃ H H H isopropyl H 1.544 CH₃ H H H n-butyl H 1.545 CH₃ H H H isobutylH 1.546 CH₃ H H H sec-butyl H 1.547 CH₃ H H H tert-butyl H 1.548 CH₃ H HH vinyl H 1.549 CH₃ H H H ethynyl H 1.550 CH₃ H H Htrimethylsilylethynyl H 1.551 CH₃ H H H CH₂OH H 1.552 CH₃ H H H CH₂OCH₃H 1.553 CH₃ H H H CH₂OCH₂CH₃ H 1.554 CH₃ H H H CH₂OCH₂OCH₃ H 1.555 CH₃ HH H CH₂OCH₂OCH₂CH₃ H 1.556 CH₃ H H H CH₂OCH₂CH₂OCH₃ H 1.557 CH₃ H H HCHO H 1.558 CH₃ H H H COCH₃ H 1.559 CH₃ H H H CO₂H H 1.560 CH₃ H H HCO₂CH₃ H 1.561 CH₃ H H H CO₂CH₂CH₃ H 1.562 CH₃ H H H CONH₂ H 1.563 CH₃ HH H CONHCH₃ H 1.564 CH₃ H H H CONHCH₂CH₃ H 1.565 CH₃ H H H CON(CH₃)₂ H1.566 CH₃ H H H CON(CH₂—CH₃)₂ H 1.567 CH₃ H H H CON(CH₃)OCH₃ H 1.568 CH₃H H H CH═NOH H 1.569 CH₃ H H H CH═N—OCH₃ H 1.570 CH₃ H H H CH═N—OCH₂CH₃H 1.571 CH₃ H H H C(CH₃)═N—OH H 1.572 CH₃ H H H C(CH₃)═N—OCH₃ H 1.573CH₃ H H H CH₂OC(O)—NHCH₃ H 1.574 CH₃ H H H CH₂NH₂ H 1.575 CH₃ H H HCH₂NHCHO H 1.576 CH₃ H H H CH₂NHC(O)CH₃ H 1.577 CH₃ H H H CH₂NHC(O)OCH₃H 1.578 CH₃ H H H NHCO₂CH₃ H 1.579 CH₃ H H H NHCO₂C(CH₃)₃ H 1.580 CH₃ HH H CH(OH)CH₃ H 1.581 CH₃ H H H CH(CH₃)OCH₃ H 1.582 CH₃ H H H CN H 1.583CH₃ H H H CH₂SCH₃ H 1.584 CH₃ H H H CH₂S(O)CH₃ H 1.585 CH₃ H H HCH₂SO₂CH₃ H 1.586 CH₃ H H H CH₂SCH₂CH₃ H 1.587 CH₃ H H H CH₂S(O)CH₂CH₃ H1.588 CH₃ H H H CH₂SO₂CH₂CH₃ H 1.589 CH₃ H H H OCH₃ H 1.590 CH₃ H H HOCH₂CH₃ H 1.591 CH₃ H H H CH(OCH₃)₂ H 1.592 CH₃ H H H CH(OCH₂CH₃)₂ H1.593 CH₃ H H H cyclopropyl H 1.594 CH₃ H H H cyclobutyl H 1.595 CH₃ H HH cyclopentyl H 1.596 CH₃ H H H cyclohexyl H 1.597 CH₃ H H H F H 1.598CH₃ H H H Cl H 1.599 CH₃ H H H Br H 1.600 CH₃ H H H I H 1.601 CH₃ H H HOH H 1.602 CH₃ H H H phenyl H 1.603 CH₃ H H H 2-acetylphenyl H 1.604 CH₃H H H 3-acetylphenyl H 1.605 CH₃ H H H 4-acetylphenyl H 1.606 CH₃ H H H2-chlorophenyl H 1.607 CH₃ H H H 3-chlorophenyl H 1.608 CH₃ H H H4-chlorophenyl H 1.609 CH₃ H H H 2-cyanophenyl H 1.610 CH₃ H H H3-cyanophenyl H 1.611 CH₃ H H H 4-cyanophenyl H 1.612 CH₃ H H H2-fluorophenyl H 1.613 CH₃ H H H 3-fluorophenyl H 1.614 CH₃ H H H4-fluorophenyl H 1.615 CH₃ H H H 2-methoxyphenyl H 1.616 CH₃ H H H3-methoxyphenyl H 1.617 CH₃ H H H 4-methoxyphenyl H 1.618 CH₃ H H H2-methylphenyl H 1.619 CH₃ H H H 3-methylphenyl H 1.620 CH₃ H H H4-methylphenyl H 1.621 CH₃ H H H 2-nitrophenyl H 1.622 CH₃ H H H3-nitrophenyl H 1.623 CH₃ H H H 4-nitrophenyl H 1.624 CH₃ H H H2-thiomethylphenyl H 1.625 CH₃ H H H 3-thiomethylphenyl H 1.626 CH₃ H HH 4-thiomethylphenyl H 1.627 CH₃ H H H 2-trifluoromethoxyphenyl H 1.628CH₃ H H H 3-trifluoromethoxyphenyl H 1.629 CH₃ H H H4-trifluoromethoxyphenyl H 1.630 CH₃ H H H 2-trifluoromethylphenyl H1.631 CH₃ H H H 3-trifluoromethylphenyl H 1.632 CH₃ H H H4-trifluoromethylphenyl H 1.633 CH₃ H H H 2,3-dichlorophenyl H 1.634 CH₃H H H 2,4-dichlorophenyl H 1.635 CH₃ H H H 2,5-dichlorophenyl H 1.636CH₃ H H H 2,6-dichlorophenyl H 1.637 CH₃ H H H 3,4-dichlorophenyl H1.638 CH₃ H H H 3,5-dichlorophenyl H 1.639 CH₃ H H H 2,3-difluorophenylH 1.640 CH₃ H H H 2,4-difluorophenyl H 1.641 CH₃ H H H2,5-difluorophenyl H 1.642 CH₃ H H H 2,6-difluorophenyl H 1.643 CH₃ H HH 3,4-difluorophenyl H 1.644 CH₃ H H H 3,5-difluorophenyl H 1.645 CH₃ HH H 2,4,6-trifluorophenyl H 1.646 CH₃ H H H 2,4-dimethylphenyl H 1.647CH₃ H H H 2,4,6-trimethylphenyl H 1.648 CH₃ H H H3,4,5-trimethoxy-phenyl H 1.649 CH₃ H H H 2-chloro-3-cyanophenyl H 1.650CH₃ H H H 2-chloro-4-cyanophenyl H 1.651 CH₃ H H H2-chloro-5-cyanophenyl H 1.652 CH₃ H H H 2-chloro-6-cyanophenyl H 1.653CH₃ H H H 3-chloro-2-cyanophenyl H 1.654 CH₃ H H H3-chloro-4-cyanophenyl H 1.655 CH₃ H H H 3-chloro-5-cyanophenyl H 1.656CH₃ H H H 5-chloro-2-cyanophenyl H 1.657 CH₃ H H H4-chloro-2-cyanophenyl H 1.658 CH₃ H H H 4-chloro-3-cyanophenyl H 1.659CH₃ H H H 2-chloro-3-fluorophenyl H 1.660 CH₃ H H H2-chloro-4-fluorophenyl H 1.661 CH₃ H H H 2-chloro-5-fluorophenyl H1.662 CH₃ H H H 2-chloro-6-fluorophenyl H 1.663 CH₃ H H H3-chloro-2-fluorophenyl H 1.664 CH₃ H H H 3-chloro-4-fluorophenyl H1.665 CH₃ H H H 3-chloro-5-fluorophenyl H 1.666 CH₃ H H H5-chloro-2-fluorophenyl H 1.667 CH₃ H H H 4-chloro-2-fluorophenyl H1.668 CH₃ H H H 4-chloro-3-fluorophenyl H 1.669 CH₃ H H H2-chloro-3-methylphenyl H 1.670 CH₃ H H H 2-chloro-4-methylphenyl H1.671 CH₃ H H H 2-chloro-5-methylphenyl H 1.672 CH₃ H H H2-chloro-6-methylphenyl H 1.673 CH₃ H H H 3-chloro-2-methylphenyl H1.674 CH₃ H H H 3-chloro-4-methylphenyl H 1.675 CH₃ H H H3-chloro-5-methylphenyl H 1.676 CH₃ H H H 5-chloro-2-methylphenyl H1.677 CH₃ H H H 4-chloro-2-methylphenyl H 1.678 CH₃ H H H4-chloro-3-methylphenyl H 1.679 CH₃ H H H 2-cyano-3-fluorophenyl H 1.680CH₃ H H H 2-cyano-4-fluorophenyl H 1.681 CH₃ H H H2-cyano-5-fluorophenyl H 1.682 CH₃ H H H 2-cyano-6-fluorophenyl H 1.683CH₃ H H H 3-cyano-2-fluorophenyl H 1.684 CH₃ H H H3-cyano-4-fluorophenyl H 1.685 CH₃ H H H 3-cyano-5-fluorophenyl H 1.686CH₃ H H H 5-cyano-2-fluorophenyl H 1.687 CH₃ H H H4-cyano-2-fluorophenyl H 1.688 CH₃ H H H 4-cyano-3-fluorophenyl H 1.689CH₃ H H H 2-fluoro-3-methylphenyl H 1.690 CH₃ H H H2-fluoro-4-methylphenyl H 1.691 CH₃ H H H 2-fluoro-5-methylphenyl H1.692 CH₃ H H H 2-fluoro-6-methylphenyl H 1.693 CH₃ H H H3-fluoro-2-methylphenyl H 1.694 CH₃ H H H 3-fluoro-4-methylphenyl H1.695 CH₃ H H H 3-fluoro-5-methylphenyl H 1.696 CH₃ H H H5-fluoro-2-methylphenyl H 1.697 CH₃ H H H 4-fluoro-2-methylphenyl H1.698 CH₃ H H H 4-fluoro-3-methylphenyl H 1.699 CH₃ H H H pyridin-2-yl H1.700 CH₃ H H H pyridin-3-yl H 1.701 CH₃ H H H pyridin-4-yl H 1.702 CH₃H H H 3-chloropyridin-2-yl H 1.703 CH₃ H H H 4-chloropyridin-2-yl H1.704 CH₃ H H H 5-chloropyridin-2-yl H 1.705 CH₃ H H H6-chloropyridin-2-yl H 1.706 CH₃ H H H 2-chloropyridin-3-yl H 1.707 CH₃H H H 4-chloropyridin-3-yl H 1.708 CH₃ H H H 5-chloropyridin-3-yl H1.709 CH₃ H H H 2-chloropyridin-4-yl H 1.710 CH₃ H H H3-chloropyridin-4-yl H 1.711 CH₃ H H H 2-chloropyridin-5-yl H 1.712 CH₃H H H 3-cyanopyridin-2-yl H 1.713 CH₃ H H H 4-cyanopyridin-2-yl H 1.714CH₃ H H H 5-cyanopyridin-2-yl H 1.715 CH₃ H H H 6-cyanopyridin-2-yl H1.716 CH₃ H H H 2-cyanopyridin-3-yl H 1.717 CH₃ H H H4-cyanopyridin-3-yl H 1.718 CH₃ H H H 5-cyanopyridin-3-yl H 1.719 CH₃ HH H 2-cyanopyridin-5-yl H 1.720 CH₃ H H H 3-fluoropyridin-2-yl H 1.721CH₃ H H H 4-fluoropyridin-2-yl H 1.722 CH₃ H H H 5-fluoropyridin-2-yl H1.723 CH₃ H H H 6-fluoropyridin-2-yl H 1.724 CH₃ H H H2-fluoropyridin-3-yl H 1.725 CH₃ H H H 4-fluoropyridin-3-yl H 1.726 CH₃H H H 5-fluoropyridin-3-yl H 1.727 CH₃ H H H 2-fluoropyridin-5-yl H1.728 CH₃ H H H 3-nitropyridin-2-yl H 1.729 CH₃ H H H4-nitropyridin-2-yl H 1.730 CH₃ H H H 5-nitropyridin-2-yl H 1.731 CH₃ HH H 6-nitropyridin-2-yl H 1.732 CH₃ H H H 2-nitropyridin-3-yl H 1.733CH₃ H H H 4-nitropyridin-3-yl H 1.734 CH₃ H H H 5-nitropyridin-3-yl H1.735 CH₃ H H H 2-nitropyridin-5-yl H 1.736 CH₃ H H H3-trifluoromethylpyridin-2-yl H 1.737 CH₃ H H H4-trifluoromethylpyridin-2-yl H 1.738 CH₃ H H H5-trifluoromethylpyridin-2-yl H 1.739 CH₃ H H H6-trifluoromethylpyridin-2-yl H 1.740 CH₃ H H H2-trifluoromethylpyridin-3-yl H 1.741 CH₃ H H H4-trifluoromethylpyridin-3-yl H 1.742 CH₃ H H H5-trifluoromethylpyridin-3-yl H 1.743 CH₃ H H H2-trifluoromethylpyridin-5-yl H 1.744 CH₃ H H H2,6-bis(trifluoromethyl)- H pyridin-3-yl 1.745 CH₃ H H H2,6-bis(trifluoromethyl)- H pyridin-4-yl 1.746 CH₃ H H H3,5-bis(trifluoromethyl)- H pyridin-2-yl 1.747 CH₃ H H H 2-thienyl H1.748 CH₃ H H H 3-thienyl H 1.749 CH₃ H H H 5-cyanothien-2-yl H 1.750CH₃ H H H 2-furyl H 1.751 CH₃ H H H 3-furyl H 1.752 CH₃ H H H1-methyl-1,2,3-triazol-4-yl H 1.753 CH₃ H H H 2-methylthiopyrimidin-4-ylH 1.754 CH₃ H H H 5-methyl-2-methyl- H thiopyrimidin-4-yl 1.755 CH₃ H HH pyrazin-2-yl H 1.756 CH₃ H H H 3,6-dimethylpyrazin-2-yl H 1.757 CH₃ HH H 3-cyanopyrazin-2-yl H 1.758 CH₃ H H H quinolin-2-yl H 1.759 CH₃ H HH 3-ethylquinolin-2-yl H 1.760 CH₃ H H H benzyl H 1.761 CH₃ H H H4-fluorobenzyl H 1.762 CH₃ H H H 4-chlorobenzyl H 1.763 CH₃ H H H4-methylbenzyl H 1.764 CH₃ H H H 2,4-dimethylbenzyl H 1.765 CH₃ H H H2,4,6-trimethylbenzyl H 1.766 CH₃ H H H H CH₃ 1.767 CH₃ H H H CH₃ CH₃1.768 CH₃ H H H CH₂CH₃ CH₃ 1.769 CH₃ H H H n-propyl CH₃ 1.770 CH₃ H H Hisopropyl CH₃ 1.771 CH₃ H H H n-butyl CH₃ 1.772 CH₃ H H H isobutyl CH₃1.773 CH₃ H H H sec-butyl CH₃ 1.774 CH₃ H H H tert-butyl CH₃ 1.775 CH₃ HH H vinyl CH₃ 1.776 CH₃ H H H ethynyl CH₃ 1.777 CH₃ H H Htrimethylsilylethynyl CH₃ 1.778 CH₃ H H H CH₂OH CH₃ 1.779 CH₃ H H HCH₂OCH₃ CH₃ 1.780 CH₃ H H H CH₂OCH₂CH₃ CH₃ 1.781 CH₃ H H H CH₂OCH₂OCH₃CH₃ 1.782 CH₃ H H H CH₂OCH₂OCH₂CH₃ CH₃ 1.783 CH₃ H H H CH₂OCH₂CH₂OCH₃CH₃ 1.784 CH₃ H H H CHO CH₃ 1.785 CH₃ H H H COCH₃ CH₃ 1.786 CH₃ H H HCO₂H CH₃ 1.787 CH₃ H H H CO₂CH₃ CH₃ 1.788 CH₃ H H H CO₂CH₂CH₃ CH₃ 1.789CH₃ H H H CONH₂ CH₃ 1.790 CH₃ H H H CONHCH₃ CH₃ 1.791 CH₃ H H HCONHCH₂CH₃ CH₃ 1.792 CH₃ H H H CON(CH₃)₂ CH₃ 1.793 CH₃ H H HCON(CH₂—CH₃)₂ CH₃ 1.794 CH₃ H H H CON(CH₃)OCH₃ CH₃ 1.795 CH₃ H H HCH═NOH CH₃ 1.796 CH₃ H H H CH═N—OCH₃ CH₃ 1.797 CH₃ H H H CH═N—OCH₂CH₃CH₃ 1.798 CH₃ H H H C(CH₃)═N—OH CH₃ 1.799 CH₃ H H H C(CH₃)═N—OCH₃ CH₃1.800 CH₃ H H H CH₂OC(O)—NHCH₃ CH₃ 1.801 CH₃ H H H CH₂NH₂ CH₃ 1.802 CH₃H H H CH₂NHCHO CH₃ 1.803 CH₃ H H H CH₂NHC(O)CH₃ CH₃ 1.804 CH₃ H H HCH₂NHC(O)OCH₃ CH₃ 1.805 CH₃ H H H NHCO₂CH₃ CH₃ 1.806 CH₃ H H HNHCO₂C(CH₃)₃ CH₃ 1.807 CH₃ H H H CH(OH)CH₃ CH₃ 1.808 CH₃ H H HCH(CH₃)OCH₃ CH₃ 1.809 CH₃ H H H CN CH₃ 1.810 CH₃ H H H CH₂SCH₃ CH₃ 1.811CH₃ H H H CH₂S(O)CH₃ CH₃ 1.812 CH₃ H H H CH₂SO₂CH₃ CH₃ 1.813 CH₃ H H HCH₂SCH₂CH₃ CH₃ 1.814 CH₃ H H H CH₂S(O)CH₂CH₃ CH₃ 1.815 CH₃ H H HCH₂SO₂CH₂CH₃ CH₃ 1.816 CH₃ H H H OCH₃ CH₃ 1.817 CH₃ H H H OCH₂CH₃ CH₃1.818 CH₃ H H H CH(OCH₃)₂ CH₃ 1.819 CH₃ H H H CH(OCH₂CH₃)₂ CH₃ 1.820 CH₃H H H Cyclopropyl CH₃ 1.821 CH₃ H H H Cyclobutyl CH₃ 1.822 CH₃ H H HCyclopentyl CH₃ 1.823 CH₃ H H H Cyclohexyl CH₃ 1.824 CH₃ H H H F CH₃1.825 CH₃ H H H Cl CH₃ 1.826 CH₃ H H H Br CH₃ 1.827 CH₃ H H H I CH₃1.828 CH₃ H H H OH CH₃ 1.829 CH₃ H H H phenyl CH₃ 1.830 CH₃ H H H2-acetylphenyl CH₃ 1.831 CH₃ H H H 3-acetylphenyl CH₃ 1.832 CH₃ H H H4-acetylphenyl CH₃ 1.833 CH₃ H H H 2-chlorophenyl CH₃ 1.834 CH₃ H H H3-chlorophenyl CH₃ 1.835 CH₃ H H H 4-chlorophenyl CH₃ 1.836 CH₃ H H H2-cyanophenyl CH₃ 1.837 CH₃ H H H 3-cyanophenyl CH₃ 1.838 CH₃ H H H4-cyanophenyl CH₃ 1.839 CH₃ H H H 2-fluorophenyl CH₃ 1.840 CH₃ H H H3-fluorophenyl CH₃ 1.841 CH₃ H H H 4-fluorophenyl CH₃ 1.842 CH₃ H H H2-methoxyphenyl CH₃ 1.843 CH₃ H H H 3-methoxyphenyl CH₃ 1.844 CH₃ H H H4-methoxyphenyl CH₃ 1.845 CH₃ H H H 2-methylphenyl CH₃ 1.846 CH₃ H H H3-methylphenyl CH₃ 1.847 CH₃ H H H 4-methylphenyl CH₃ 1.848 CH₃ H H H2-nitrophenyl CH₃ 1.849 CH₃ H H H 3-nitrophenyl CH₃ 1.850 CH₃ H H H4-nitrophenyl CH₃ 1.851 CH₃ H H H 2-thiomethylphenyl CH₃ 1.852 CH₃ H H H3-thiomethylphenyl CH₃ 1.853 CH₃ H H H 4-thiomethylphenyl CH₃ 1.854 CH₃H H H 2-trifluoromethoxyphenyl CH₃ 1.855 CH₃ H H H3-trifluoromethoxyphenyl CH₃ 1.856 CH₃ H H H 4-trifluoromethoxyphenylCH₃ 1.857 CH₃ H H H 2-trifluoromethylphenyl CH₃ 1.858 CH₃ H H H3-trifluoromethylphenyl CH₃ 1.859 CH₃ H H H 4-trifluoromethylphenyl CH₃1.860 CH₃ H H H 2,3-dichlorophenyl CH₃ 1.861 CH₃ H H H2,4-dichlorophenyl CH₃ 1.862 CH₃ H H H 2,5-dichlorophenyl CH₃ 1.863 CH₃H H H 2,6-dichlorophenyl CH₃ 1.864 CH₃ H H H 3,4-dichlorophenyl CH₃1.865 CH₃ H H H 3,5-dichlorophenyl CH₃ 1.866 CH₃ H H H2,3-difluorophenyl CH₃ 1.867 CH₃ H H H 2,4-difluorophenyl CH₃ 1.868 CH₃H H H 2,5-difluorophenyl CH₃ 1.869 CH₃ H H H 2,6-difluorophenyl CH₃1.870 CH₃ H H H 3,4-difluorophenyl CH₃ 1.871 CH₃ H H H3,5-difluorophenyl CH₃ 1.872 CH₃ H H H 2,4,6-trifluorophenyl CH₃ 1.873CH₃ H H H 2,4-dimethylphenyl CH₃ 1.874 CH₃ H H H 2,4,6-trimethylphenylCH₃ 1.875 CH₃ H H H 3,4,5-trimethoxyphenyl CH₃ 1.876 CH₃ H H H2-chloro-3-cyanophenyl CH₃ 1.877 CH₃ H H H 2-chloro-4-cyanophenyl CH₃1.878 CH₃ H H H 2-chloro-5-cyanophenyl CH₃ 1.879 CH₃ H H H2-chloro-6-cyanophenyl CH₃ 1.880 CH₃ H H H 3-chloro-2-cyanophenyl CH₃1.881 CH₃ H H H 3-chloro-4-cyanophenyl CH₃ 1.882 CH₃ H H H3-chloro-5-cyanophenyl CH₃ 1.883 CH₃ H H H 5-chloro-2-cyanophenyl CH₃1.884 CH₃ H H H 4-chloro-2-cyanophenyl CH₃ 1.885 CH₃ H H H4-chloro-3-cyanophenyl CH₃ 1.886 CH₃ H H H 2-chloro-3-fluorophenyl CH₃1.887 CH₃ H H H 2-chloro-4-fluorophenyl CH₃ 1.888 CH₃ H H H2-chloro-5-fluorophenyl CH₃ 1.889 CH₃ H H H 2-chloro-6-fluorophenyl CH₃1.890 CH₃ H H H 3-chloro-2-fluorophenyl CH₃ 1.891 CH₃ H H H3-chloro-4-fluorophenyl CH₃ 1.892 CH₃ H H H 3-chloro-5-fluorophenyl CH₃1.893 CH₃ H H H 5-chloro-2-fluorophenyl CH₃ 1.894 CH₃ H H H4-chloro-2-fluorophenyl CH₃ 1.895 CH₃ H H H 4-chloro-3-fluorophenyl CH₃1.896 CH₃ H H H 2-chloro-3-methylphenyl CH₃ 1.897 CH₃ H H H2-chloro-4-methylphenyl CH₃ 1.898 CH₃ H H H 2-chloro-5-methylphenyl CH₃1.899 CH₃ H H H 2-chloro-6-methylphenyl CH₃ 1.900 CH₃ H H H3-chloro-2-methylphenyl CH₃ 1.901 CH₃ H H H 3-chloro-4-methylphenyl CH₃1.902 CH₃ H H H 3-chloro-5-methylphenyl CH₃ 1.903 CH₃ H H H5-chloro-2-methylphenyl CH₃ 1.904 CH₃ H H H 4-chloro-2-methylphenyl CH₃1.905 CH₃ H H H 4-chloro-3-methylphenyl CH₃ 1.906 CH₃ H H H2-cyano-3-fluorophenyl CH₃ 1.907 CH₃ H H H 2-cyano-4-fluorophenyl CH₃1.908 CH₃ H H H 2-cyano-5-fluorophenyl CH₃ 1.909 CH₃ H H H2-cyano-6-fluorophenyl CH₃ 1.910 CH₃ H H H 3-cyano-2-fluorophenyl CH₃1.911 CH₃ H H H 3-cyano-4-fluorophenyl CH₃ 1.912 CH₃ H H H3-cyano-5-fluorophenyl CH₃ 1.913 CH₃ H H H 5-cyano-2-fluorophenyl CH₃1.914 CH₃ H H H 4-cyano-2-fluorophenyl CH₃ 1.915 CH₃ H H H4-cyano-3-fluorophenyl CH₃ 1.916 CH₃ H H H 2-fluoro-3-methylphenyl CH₃1.917 CH₃ H H H 2-fluoro-4-methylphenyl CH₃ 1.918 CH₃ H H H2-fluoro-5-methylphenyl CH₃ 1.919 CH₃ H H H 2-fluoro-6-methylphenyl CH₃1.920 CH₃ H H H 3-fluoro-2-methylphenyl CH₃ 1.921 CH₃ H H H3-fluoro-4-methylphenyl CH₃ 1.922 CH₃ H H H 3-fluoro-5-methylphenyl CH₃1.923 CH₃ H H H 5-fluoro-2-methylphenyl CH₃ 1.924 CH₃ H H H4-fluoro-2-methylphenyl CH₃ 1.925 CH₃ H H H 4-fluoro-3-methylphenyl CH₃1.926 CH₃ H H H pyridin-2-yl CH₃ 1.927 CH₃ H H H pyridin-3-yl CH₃ 1.928CH₃ H H H pyridin-4-yl CH₃ 1.929 CH₃ H H H 3-chloropyridin-2-yl CH₃1.930 CH₃ H H H 4-chloropyridin-2-yl CH₃ 1.931 CH₃ H H H5-chloropyridin-2-yl CH₃ 1.932 CH₃ H H H 6-chloropyridin-2-yl CH₃ 1.933CH₃ H H H 2-chloropyridin-3-yl CH₃ 1.934 CH₃ H H H 4-chloropyridin-3-ylCH₃ 1.935 CH₃ H H H 5-chloropyridin-3-yl CH₃ 1.936 CH₃ H H H2-chloropyridin-4-yl CH₃ 1.937 CH₃ H H H 3-chloropyridin-4-yl CH₃ 1.938CH₃ H H H 2-chloropyridin-5-yl CH₃ 1.939 CH₃ H H H 3-cyanopyridin-2-ylCH₃ 1.940 CH₃ H H H 4-cyanopyridin-2-yl CH₃ 1.941 CH₃ H H H5-cyanopyridin-2-yl CH₃ 1.942 CH₃ H H H 6-cyanopyridin-2-yl CH₃ 1.943CH₃ H H H 2-cyanopyridin-3-yl CH₃ 1.944 CH₃ H H H 4-cyanopyridin-3-ylCH₃ 1.945 CH₃ H H H 5-cyanopyridin-3-yl CH₃ 1.946 CH₃ H H H2-cyanopyridin-5-yl CH₃ 1.947 CH₃ H H H 3-fluoropyridin-2-yl CH₃ 1.948CH₃ H H H 4-fluoropyridin-2-yl CH₃ 1.949 CH₃ H H H 5-fluoropyridin-2-ylCH₃ 1.950 CH₃ H H H 6-fluoropyridin-2-yl CH₃ 1.951 CH₃ H H H2-fluoropyridin-3-yl CH₃ 1.952 CH₃ H H H 4-fluoropyridin-3-yl CH₃ 1.953CH₃ H H H 5-fluoropyridin-3-yl CH₃ 1.954 CH₃ H H H 2-fluoropyridin-5-ylCH₃ 1.955 CH₃ H H H 3-nitropyridin-2-yl CH₃ 1.956 CH₃ H H H4-nitropyridin-2-yl CH₃ 1.957 CH₃ H H H 5-nitropyridin-2-yl CH₃ 1.958CH₃ H H H 6-nitropyridin-2-yl CH₃ 1.959 CH₃ H H H 2-nitropyridin-3-ylCH₃ 1.960 CH₃ H H H 4-nitropyridin-3-yl CH₃ 1.961 CH₃ H H H5-nitropyridin-3-yl CH₃ 1.962 CH₃ H H H 2-nitropyridin-5-yl CH₃ 1.963CH₃ H H H 3-trifluoromethylpyridin-2-yl CH₃ 1.964 CH₃ H H H4-trifluoromethylpyridin-2-yl CH₃ 1.965 CH₃ H H H5-trifluoromethylpyridin-2-yl CH₃ 1.966 CH₃ H H H6-trifluoromethylpyridin-2-yl CH₃ 1.967 CH₃ H H H2-trifluoromethylpyridin-3-yl CH₃ 1.968 CH₃ H H H4-trifluoromethylpyridin-3-yl CH₃ 1.969 CH₃ H H H5-trifluoromethylpyridin-3-yl CH₃ 1.970 CH₃ H H H2-trifluoromethylpyridin-5-yl CH₃ 1.971 CH₃ H H H2,6-bis(trifluoromethyl)- CH₃ pyridin-3-yl 1.972 CH₃ H H H2,6-bis(trifluoromethyl)- CH₃ pyridin-4-yl 1.973 CH₃ H H H3,5-bis(trifluoromethyl)- CH₃ pyridin-2-yl 1.974 CH₃ H H H 2-thienyl CH₃1.975 CH₃ H H H 3-thienyl CH₃ 1.976 CH₃ H H H 5-cyanothien-2-yl CH₃1.977 CH₃ H H H 2-furyl CH₃ 1.978 CH₃ H H H 3-furyl CH₃ 1.979 CH₃ H H H1-methyl-1,2,3-triazol-4-yl CH₃ 1.980 CH₃ H H H2-methylthiopyrimidin-4-yl CH₃ 1.981 CH₃ H H H 5-methyl-2-methyl- CH₃thiopyrimidin-4-yl 1.982 CH₃ H H H pyrazin-2-yl CH₃ 1.983 CH₃ H H H3,6-dimethylpyrazin-2-yl CH₃ 1.984 CH₃ H H H 3-cyanopyrazin-2-yl CH₃1.985 CH₃ H H H quinolin-2-yl CH₃ 1.986 CH₃ H H H 3-ethylquinolin-2-ylCH₃ 1.987 CH₃ H H H benzyl CH₃ 1.988 CH₃ H H H 4-fluorobenzyl CH₃ 1.989CH₃ H H H 4-chlorobenzyl CH₃ 1.990 CH₃ H H H 4-methylbenzyl CH₃ 1.991CH₃ H H H 2,4-dimethylbenzyl CH₃ 1.992 CH₃ H H H 2,4,6-trimethylbenzylCH₃ 1.993 CH₃ H H H H CH₂OH 1.994 CH₃ H H H H CH₂OCH₃ 1.995 CH₃ H H H HCH₂OCH₂CH₃ 1.996 CH₃ H H H H CHO 1.997 CH₃ H H H H COCH₃ 1.998 CH₃ H H HH CO₂H 1.999 CH₃ H H H H CO₂CH₃ 1.1000 CH₃ H H H H CO₂CH₂CH₃ 1.1001 CH₃H H H H CONH₂ 1.1002 CH₃ H H H H CONHCH₃ 1.1003 CH₃ H H H H CONHCH₂CH₃1.1004 CH₃ H H H H CON(CH₃)₂ 1.1005 CH₃ H H H H CON—(CH₂CH₃)₂ 1.1006 CH₃H H H H CON(CH₃)O—CH₃ 1.1007 CH₃ H H H H CH═NOH 1.1008 CH₃ H H H HCH═NOCH₃ 1.1009 CH₃ H H H H CH═NOCH₂—CH₃ 1.1010 CH₃ H H H H C(CH₃)═NOH1.1011 CH₃ H H H H C(CH₃)═NO—CH₃ 1.1012 CH₃ H H H H CH₂OC(O)NH—CH₃1.1013 CH₃ H H H H CH₂NH₂ 1.1014 CH₃ H H H H CH₂NHCHO 1.1015 CH₃ H H H HCH₂NHC(O)—CH₃ 1.1016 CH₃ H H H H CH₂NHC(O)OCH₃ 1.1017 CH₃ H H H HNHCO₂CH₃ 1.1018 CH₃ H H H H NHCO₂—C(CH₃)₃ 1.1019 CH₃ H H H H CH(OH)CH₃1.1020 CH₃ H H H H CH(CH₃)OCH₃ 1.1021 CH₃ H H H H CN 1.1022 CH₃ H H H HCH₂SCH₃ 1.1023 CH₃ H H H H CH₂S(O)CH₃ 1.1024 CH₃ H H H H CH₂SO₂CH₃1.1025 CH₃ H H H H CH₂SCH₂CH₃ 1.1026 CH₃ H H H H CH₂S(O)CH₂—CH₃ 1.1027CH₃ H H H H CH₂SO₂CH₂—CH₃ 1.1028 CH₃ H H H H OCH₃ 1.1029 CH₃ H H H HOCH₂CH₃ 1.1030 CH₃ H H H H CH(OCH₃)₂ 1.1031 CH₃ H H H H CH—(OCH₂CH₃)₂1.1032 CH₃ H H H H CH₂CH₃ 1.1033 CH₃ H H H H CH₂CH₂CH₃ 1.1034 CH₃ H H HH CH(CH₃)₂ 1.1035 CH₃ H H H H C(CH₃)₃ 1.1036 CH₃ H H H H CH₂CH(CH₃)₂1.1037 CH₃ H H H H CH₂C(CH₃)₃ 1.1038 CH₃ H H H H CH₂CN 1.1039 CH₃ H H HH cyclopropyl 1.1040 CH₃ H H H H cyclobutyl 1.1041 CH₃ H H H Hcyclopentyl 1.1042 CH₃ H H H H cyclohexyl 1.1043 CH₃ H H H HCH₂-cyclopropyl 1.1044 CH₃ H H H H benzyl 1.1045 CH₃ H H H H CH₂CF₃1.1046 CH₃ CH₃ H H CH₃ CH₃ 1.1047 H H Cl Cl H H 1.1048 H H Cl Cl H CH₃1.1049 CH₃ H Cl Cl H CH₃ 1.1050 H H Br Br H H 1.1051 H H Br Br H CH₃1.1052 CH₃ H Br Br H CH₃ 1.1053 H H OH OH H H 1.1054 H H OH OH H CH₃1.1055 CH₃ H OH OH H CH₃ 1.1056 H H —O—C(CH₃)₂—O— H H 1.1057 H H—O—C(CH₃)₂—O— H CH₃ 1.1058 CH₃ H —O—C(CH₃)₂—O— H CH₃ 1.1059 H R⁷ and R⁸form unit ═O H H H 1.1060 H R⁷ and R⁸ form unit ═O H H CH₃ 1.1061 CH₃ R⁷and R⁸ form unit ═O H H H 1.1062 CH₃ R⁷ and R⁸ form unit ═O H H CH₃1.1063 H R⁷ and R⁸ form unit ═NOCH₃ H H H 1.1064 H R⁷ and R⁸ form unit═NOCH₃ H H CH₃ 1.1065 CH₃ R⁷ and R⁸ form unit ═NOCH₃ H H H 1.1066 CH₃ R⁷and R⁸ form unit ═NOCH₃ H H CH₃ 1.1067 H R⁷ and R⁸ form unit ═NOCH₂CH₃ HH H 1.1068 H R⁷ and R⁸ form unit ═NOCH₂CH₃ H H CH₃ 1.1069 CH₃ R⁷ and R⁸form unit ═NOCH₂CH₃ H H H 1.1070 CH₃ R⁷ and R⁸ form unit ═NOCH₂CH₃ H HCH₃ 1.1071 H H H —O—(CH₂)₂—O— H 1.1072 H H H —O—(CH₂)₂—O— CH₃ 1.1073 CH₃H H —O—(CH₂)₂—O— H 1.1074 CH₃ H H —O—(CH₂)₂—O— CH₃ 1.1075 H H H—O—(CH₂)₃—O— H 1.1076 H H H —O—(CH₂)₃—O— CH₃ 1.1077 CH₃ H H —O—(CH₂)₃—O—H 1.1078 CH₃ H H —O—(CH₂)₃—O— CH₃

Table 2 covers compounds of formula (A), wherein R¹ is ethyl, R² and R⁴are methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 3 covers compounds of formula (A), wherein R¹ and R⁴ are ethyl, R²is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 4 covers compounds of formula (A), wherein R¹, R² and R⁴ areethyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ areas defined in Table 1.

Table 5 covers compounds of formula (A), wherein R¹ and R² are methyl,R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are asdefined in Table 1.

Table 6 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 7 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 8 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 9 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 10 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is ethynyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 11 covers compounds of formula (A), wherein R¹ and R² are methyl,R⁴ is vinyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 12 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 13 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 14 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 15 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 16 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 17 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is ethynyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 18 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R⁴ is vinyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 19 covers compounds of formula (A), wherein R¹ is ethynyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 20 covers compounds of formula (A), wherein R¹ is ethynyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 21 covers compounds of formula (A), wherein R¹ is ethynyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 22 covers compounds of formula (A), wherein R¹ is ethynyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 23 covers compounds of formula (A), wherein R¹ is ethynyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 24 covers compounds of formula (A), wherein R¹ and R⁴ are ethynyl,R² is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 25 covers compounds of formula (A), wherein R¹ is vinyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 26 covers compounds of formula (A), wherein R¹ is vinyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 27 covers compounds of formula (A), wherein R¹ is vinyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 28 covers compounds of formula (A), wherein R¹ is vinyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 29 covers compounds of formula (A), wherein R¹ is vinyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 30 covers compounds of formula (A), wherein R¹ and R⁴ are vinyl,R² is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 31 covers compounds of formula (A), wherein R¹ is methyl, R², R³,R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are asdefined in Table 1.

Table 32 covers compounds of formula (A), wherein R¹ is methyl, R² ismethoxy, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 33 covers compounds of formula (A), wherein R¹ is methyl, R² istrifluoromethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 34 covers compounds of formula (A), wherein R¹ is methyl, R² isethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 35 covers compounds of formula (A), wherein R¹ is methyl, R² isethynyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 36 covers compounds of formula (A), wherein R¹ is methyl, R² isvinyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 37 covers compounds of formula (A), wherein R¹ is methyl, R² ischlorine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 38 covers compounds of formula (A), wherein R¹ is methyl, R² isbromine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 39 covers compounds of formula (A), wherein R¹ is methyl, R² isiodine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 40 covers compounds of formula (A), wherein R¹ is ethyl, R², R³,R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are asdefined in Table 1.

Table 41 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethoxy, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 42 covers compounds of formula (A), wherein R¹ is ethyl, R² istrifluoromethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 43 covers compounds of formula (A), wherein R¹ is ethyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 44 covers compounds of formula (A), wherein R¹ is ethyl, R² isethynyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 45 covers compounds of formula (A), wherein R¹ is ethyl, R² isvinyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 46 covers compounds of formula (A), wherein R¹ is ethyl, R² ischlorine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 47 covers compounds of formula (A), wherein R¹ is ethyl, R² isbromine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 48 covers compounds of formula (A), wherein R¹ is ethyl, R² isiodine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹are as defined in Table 1.

Table 49 covers compounds of formula (A), wherein R¹ and R⁴ are methyl,R² is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 50 covers compounds of formula (A), wherein R¹ and R⁴ are methyl,R² is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 51 covers compounds of formula (A), wherein R¹ and R⁴ are methyl,R² is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 52 covers compounds of formula (A), wherein R¹ is methyl, R² ischlorine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 53 covers compounds of formula (A), wherein R¹ is methyl, R² isbromine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 54 covers compounds of formula (A), wherein R¹ is methyl, R² isiodine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶, R⁷,R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 55 covers compounds of formula (A), wherein R¹ and R⁴ are ethyl,R² is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 56 covers compounds of formula (A), wherein R¹ and R⁴ are ethyl,R² is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 57 covers compounds of formula (A), wherein R¹ and R⁴ are ethyl,R² is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 58 covers compounds of formula (A), wherein R¹ is methyl, R² ischlorine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 59 covers compounds of formula (A), wherein R¹ is methyl, R² isbromine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 60 covers compounds of formula (A), wherein R¹ is ethyl, R² ischlorine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 61 covers compounds of formula (A), wherein R¹ is ethyl, R² isbromine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 62 covers compounds of formula (A), wherein R¹ and R⁴ are methyl,R² is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 63 covers compounds of formula (A), wherein R¹ is methyl, R² ismethoxy, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 64 covers compounds of formula (A), wherein R¹ and R⁴ are ethyl,R² is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, andR¹¹ are as defined in Table 1.

Table 65 covers compounds of formula (A), wherein R¹, R², R³ and R⁴ aremethyl, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are asdefined in Table 1.

Table 66 covers compounds of formula (A), wherein R¹ is difluoromethoxy,R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 67 covers compounds of formula (A), wherein R¹ is difluoromethoxy,R² is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸,R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 68 covers compounds of formula (A), wherein R¹ istrifluoromethoxy, R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen andR⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 67 covers compounds of formula (A), wherein R¹ istrifluoromethoxy, R² is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogenand R⁶, R⁷, R⁸, R⁹, R¹⁰, and R¹¹ are as defined in Table 1.

Table 70 covers compounds of formula (A), wherein R¹ is cyclopropyl, R²and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹, R¹⁰,and R¹¹ are as defined in Table 1.

Table 71 covers compounds of formula (A), wherein R¹ is cyclopropyl, R²is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁷, R⁸, R⁹,R¹⁰, and R¹¹ are as defined in Table 1.

Table 72 covers compounds of formula (A), wherein R¹ and R² are methyl,R³, R⁵ and R¹² are hydrogen, R⁴ is cyclopropyl and R⁶, R⁷, R⁸, R⁹, R¹⁰,and R¹¹ are as defined in Table 1.

Table 73 covers compounds of formula (A), wherein R¹ and R² are ethyl,R³, R⁵ and R¹² are hydrogen, R⁴ is cyclopropyl and R⁶, R⁷, R⁸, R⁹, R¹⁰,and R¹¹ are as defined in Table 1.

Table 74 covers compounds of formula (AH)

wherein R¹, R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

TABLE 74 R⁶ R⁸ R⁹ R¹¹ 74.001 H H H H 74.002 H H H CH₃ 74.003 H H H CH₂OH74.004 H H H CH₂OCH₃ 74.005 H H H CH₂OCH₂CH₃ 74.006 H H H CH₂OCH₂OCH₃74.007 H H H CH₂OCH₂OCH₂CH₃ 74.007 H H H CH₂OCH₂CO₂CH₃ 74.008 H H HCH₂OCH₂CO₂CH₂CH₃ 74.009 H H H CH₂OCH₂CN 74.010 H H H CH(OH)CH₃ 74.011 HH H CH(CH₃)OCH₃ 74.012 H H H CH(CH₃)OCH₂CH₃ 74.013 H H H CHO 74.014 H HH COCH₃ 74.015 H H H CH₂COCH₃ 74.016 H H H CH₂CH₂COCH₃ 74.017 H H H CO₂H74.018 H H H CO₂CH₃ 74.019 H H H CO₂CH₂CH₃ 74.020 H H H CH₂CO₂CH₃ 74.021H H H CH₂CO₂CH₂CH₃ 74.022 H H H CH₂CH₂CO₂CH₃ 74.023 H H HCH₂CH₂CO₂CH₂CH₃ 74.024 H H H CONH₂ 74.025 H H H CONHCH₃ 74.026 H H HCONHCH₂CH₃ 74.027 H H H CON(CH₃)₂ 74.028 H H H CON(CH₂CH₃)₂ 74.029 H H HCON(CH₃)OCH₃ 74.030 H H H CH═NOH 74.031 H H H CH═NOCH₃ 74.032 H H HCH═NOCH₂CH₃ 74.033 H H H C(CH₃)═NOH 74.034 H H H C(CH₃)═NOCH₃ 74.035 H HH CH₂OC(O)CH₃ 74.036 H H H CH₂OC(O)CH₂CH₃ 74.037 H H H CH₂OC(O)CH(CH₃)₂74.038 H H H CH₂OC(O)C(CH₃)₃ 74.039 H H H CH₂OC(O)NHCH₃ 74.040 H H HCH₂OC(O)NHCH₂CH₃ 74.041 H H H CH₂OC(O)NHCH₂CH₂CH₃ 74.042 H H HCH₂OC(O)NHC(CH₃)₃ 74.043 H H H CH₂NH₂ 74.044 H H H CH₂NHCHO 74.045 H H HCH₂NHC(O)CH₃ 74.046 H H H CH₂NHC(O)OCH₃ 74.047 H H H NHCO₂CH₃ 74.048 H HH NHCO₂C(CH₃)₃ 74.049 H H H CN 74.050 H H H CH₂SCH₃ 74.051 H H HCH₂SCH₂CH₃ 74.052 H H H CH₂SCH₂CH₂CH₃ 74.053 H H H CH₂SCH(CH₃)₂ 74.054 HH H CH₂S(O)CH₃ 74.055 H H H CH₂SO₂CH₃ 74.056 H H H CH₂SCH₂CH₃ 74.057 H HH CH₂S(O)CH₂CH₃ 74.058 H H H CH₂SO₂CH₂CH₃ 74.059 H H H OCH₃ 74.060 H H HOCH₂CH₃ 74.061 H H H CH(OCH₃)₂ 74.062 H H H CH(OCH₂CH₃)₂ 74.063 H H H1,3-dioxolan-2-yl 74.064 H H H 1,3-dioxan-2-yl 74.065 H H H5,5-dimethyl-1,3-dioxan-2-yl 74.066 H H H CH₂CH₃ 74.067 H H H n-propyl74.068 H H H isopropyl 74.069 H H H n-butyl 74.070 H H H isobutyl 74.071H H H sec-butyl 74.072 H H H tert-butyl 74.073 H H H n-pentyl 74.074 H HH neopentyl 74.075 H H H n-hexyl 74.076 H H H n-heptyl 74.077 H H HCH₂CN 74.078 H H H cyclopropyl 74.079 H H H cyclobutyl 74.080 H H Hcyclopentyl 74.081 H H H cyclohexyl 74.082 H H H CH₂-cyclopropyl 74.083H H H benzyl 74.084 H H H CH₂CF₃ 74.085 H H H CH₂F 74.086 H H H CHF₂74.087 H H H CF₃ 74.088 H H CH₃ H 74.089 H H CH₂CH₃ H 74.090 H Hn-propyl H 74.091 H H isopropyl H 74.092 H H n-butyl H 74.093 H Hisobutyl H 74.094 H H sec-butyl H 74.095 H H tert-butyl H 74.096 H Hvinyl H 74.097 H H ethynyl H 74.098 H H trimethylsilylethynyl H 74.099 HH CH₂OH H 74.100 H H CH₂OCH₃ H 74.101 H H CH₂OCH₂CH₃ H 74.102 H HCH₂OCH₂OCH₃ H 74.103 H H CH₂OCH₂OCH₂CH₃ H 74.104 H H CH₂OCH₂CH₂OCH₃ H74.105 H H CHO H 74.106 H H COCH₃ H 74.107 H H CO₂H H 74.108 H H CO₂CH₃H 74.109 H H CO₂CH₂CH₃ H 74.110 H H CONH₂ H 74.111 H H CONHCH₃ H 74.112H H CONHCH₂CH₃ H 74.113 H H CON(CH₃)₂ H 74.114 H H CON(CH₂—CH₃)₂ H74.115 H H CON(CH₃)OCH₃ H 74.116 H H CH═NOH H 74.117 H H CH═N—OCH₃ H74.118 H H CH═N—OCH₂CH₃ H 74.119 H H C(CH₃)═N—OH H 74.120 H HC(CH₃)═N—OCH₃ H 74.121 H H CH₂OC(O)—NHCH₃ H 74.122 H H CH₂NH₂ H 74.123 HH CH₂NHCHO H 74.124 H H CH₂NHC(O)CH₃ H 74.125 H H CH₂NHC(O)OCH₃ H 74.126H H CH(OH)CH₃ H 74.127 H H CH(CH₃)OCH₃ H 74.128 H H CN H 74.129 H HCH₂SCH₃ H 74.130 H H CH₂S(O)CH₃ H 74.131 H H CH₂SO₂CH₃ H 74.132 H HCH₂SCH₂CH₃ H 74.133 H H CH₂S(O)CH₂CH₃ H 74.134 H H CH₂SO₂CH₂CH₃ H 74.135H H OCH₃ H 74.136 H H OCH₂CH₃ H 74.137 H H CH(OCH₃)₂ H 74.138 H HCH(OCH₂CH₃)₂ H 74.139 H H cyclopropyl H 74.140 H H cyclobutyl H 74.141 HH cyclopentyl H 74.142 H H cyclohexyl H 74.143 H H F H 74.144 H H Cl H74.145 H H Br H 74.146 H H I H 74.147 H H phenyl H 74.148 H H2-acetylphenyl H 74.149 H H 3-acetylphenyl H 74.150 H H 4-acetylphenyl H74.151 H H 2-chlorophenyl H 74.152 H H 3-chlorophenyl H 74.153 H H4-chlorophenyl H 74.154 H H 2-cyanophenyl H 74.155 H H 3-cyanophenyl H74.156 H H 4-cyanophenyl H 74.157 H H 2-fluorophenyl H 74.158 H H3-fluorophenyl H 74.159 H H 4-fluorophenyl H 74.160 H H 2-methoxyphenylH 74.161 H H 3-methoxyphenyl H 74.162 H H 4-methoxyphenyl H 74.163 H H2-methylphenyl H 74.164 H H 3-methylphenyl H 74.165 H H 4-methylphenyl H74.166 H H 2-nitrophenyl H 74.167 H H 3-nitrophenyl H 74.168 H H4-nitrophenyl H 74.169 H H 2-thiomethylphenyl H 74.170 H H3-thiomethylphenyl H 74.171 H H 4-thiomethylphenyl H 74.172 H H2-trifluoromethoxyphenyl H 74.173 H H 3-trifluoromethoxyphenyl H 74.174H H 4-trifluoromethoxyphenyl H 74.175 H H 2-trifluoromethylphenyl H74.176 H H 3-trifluoromethylphenyl H 74.177 H H 4-trifluoromethylphenylH 74.178 H H 2,3-dichlorophenyl H 74.179 H H 2,4-dichlorophenyl H 74.180H H 2,5-dichlorophenyl H 74.181 H H 2,6-dichlorophenyl H 74.182 H H3,4-dichlorophenyl H 74.183 H H 3,5-dichlorophenyl H 74.184 H H2,3-difluorophenyl H 74.185 H H 2,4-difluorophenyl H 74.186 H H2,5-difluorophenyl H 74.187 H H 2,6-difluorophenyl H 74.188 H H3,4-difluorophenyl H 74.189 H H 3,5-difluorophenyl H 74.190 H H2,4,6-trifluorophenyl H 74.191 H H 2,4-dimethylphenyl H 74.192 H H2,4,6-trimethylphenyl H 74.193 H H 3,4,5-trimethoxyphenyl H 74.194 H H2-chloro-3-cyanophenyl H 74.195 H H 2-chloro-4-cyanophenyl H 74.196 H H2-chloro-5-cyanophenyl h 74.197 H H 2-chloro-6-cyanophenyl H 74.198 H H3-chloro-2-cyanophenyl H 74.199 H H 3-chloro-4-cyanophenyl H 74.200 H H3-chloro-5-cyanophenyl H 74.201 H H 5-chloro-2-cyanophenyl H 74.202 H H4-chloro-2-cyanophenyl H 74.203 H H 4-chloro-3-cyanophenyl H 74.204 H H2-chloro-3-fluorophenyl H 74.205 H H 2-chloro-4-fluorophenyl H 74.206 HH 2-chloro-5-fluorophenyl H 74.207 H H 2-chloro-6-fluorophenyl H 74.208H H 3-chloro-2-fluorophenyl H 74.209 H H 3-chloro-4-fluorophenyl H74.210 H H 3-chloro-5-fluorophenyl H 74.211 H H 5-chloro-2-fluorophenylH 74.212 H H 4-chloro-2-fluorophenyl H 74.213 H H4-chloro-3-fluorophenyl H 74.214 H H 2-chloro-3-methylphenyl H 74.215 HH 2-chloro-4-methylphenyl H 74.216 H H 2-chloro-5-methylphenyl H 74.217H H 2-chloro-6-methylphenyl H 74.218 H H 3-chloro-2-methylphenyl H74.219 H H 3-chloro-4-methylphenyl H 74.220 H H 3-chloro-5-methylphenylH 74.221 H H 5-chloro-2-methylphenyl H 74.222 H H4-chloro-2-methylphenyl H 74.223 H H 4-chloro-3-methylphenyl H 74.224 HH 2-cyano-3-fluorophenyl H 74.225 H H 2-cyano-4-fluorophenyl H 74.226 HH 2-cyano-5-fluorophenyl H 74.227 H H 2-cyano-6-fluorophenyl H 74.228 HH 3-cyano-2-fluorophenyl H 74.229 H H 3-cyano-4-fluorophenyl H 74.230 HH 3-cyano-5-fluorophenyl H 74.231 H H 5-cyano-2-fluorophenyl H 74.232 HH 4-cyano-2-fluorophenyl H 74.233 H H 4-cyano-3-fluorophenyl H 74.234 HH 2-fluoro-3-methylphenyl H 74.235 H H 2-fluoro-4-methylphenyl H 74.236H H 2-fluoro-5-methylphenyl H 74.237 H H 2-fluoro-6-methylphenyl H74.238 H H 3-fluoro-2-methylphenyl H 74.239 H H 3-fluoro-4-methylphenylH 74.240 H H 3-fluoro-5-methylphenyl H 74.241 H H5-fluoro-2-methylphenyl H 74.242 H H 4-fluoro-2-methylphenyl H 74.243 HH 4-fluoro-3-methylphenyl H 74.244 H H pyridin-2-yl H 74.245 H Hpyridin-3-yl H 74.246 H H pyridin-4-yl H 74.247 H H 3-chloropyridin-2-ylH 74.248 H H 4-chloropyridin-2-yl H 74.249 H H 5-chloropyridin-2-yl H74.250 H H 6-chloropyridin-2-yl H 74.251 H H 2-chloropyridin-3-yl H74.252 H H 4-chloropyridin-3-yl H 74.253 H H 5-chloropyridin-3-yl H74.254 H H 2-chloropyridin-4-yl H 74.255 H H 3-chloropyridin-4-yl H74.256 H H 2-chloropyridin-5-yl H 74.257 H H 3-cyanopyridin-2-yl H74.258 H H 4-cyanopyridin-2-yl H 74.259 H H 5-cyanopyridin-2-yl H 74.260H H 6-cyanopyridin-2-yl H 74.261 H H 2-cyanopyridin-3-yl H 74.262 H H4-cyanopyridin-3-yl H 74.263 H H 5-cyanopyridin-3-yl H 74.264 H H2-cyanopyridin-5-yl H 74.265 H H 3-fluoropyridin-2-yl H 74.266 H H4-fluoropyridin-2-yl H 74.267 H H 5-fluoropyridin-2-yl H 74.268 H H6-fluoropyridin-2-yl H 74.269 H H 2-fluoropyridin-3-yl H 74.270 H H4-fluoropyridin-3-yl H 74.271 H H 5-fluoropyridin-3-yl H 74.272 H H2-fluoropyridin-5-yl H 74.273 H H 3-nitropyridin-2-yl H 74.274 H H4-nitropyridin-2-yl H 74.275 H H 5-nitropyridin-2-yl H 74.276 H H6-nitropyridin-2-yl H 74.277 H H 2-nitropyridin-3-yl H 74.278 H H4-nitropyridin-3-yl H 74.279 H H 5-nitropyridin-3-yl H 74.280 H H2-nitropyridin-5-yl H 74.281 H H 3-trifluoromethylpyridin-2-yl H 74.282H H 4-trifluoromethylpyridin-2-yl H 74.283 H H5-trifluoromethylpyridin-2-yl H 74.284 H H 6-trifluoromethylpyridin-2-ylH 74.285 H H 2-trifluoromethylpyridin-3-yl H 74.286 H H4-trifluoromethylpyridin-3-yl H 74.287 H H 5-trifluoromethylpyridin-3-ylH 74.288 H H 2-trifluoromethylpyridin-5-yl H 74.289 H H2,6-bis(trifluoromethyl)pyridin-3-yl H 74.290 H H2,6-bis(trifluoromethyl)pyridin-4-yl H 74.291 H H3,5-bis(trifluoromethyl)pyridin-2-yl H 74.292 H H 2-thienyl H 74.293 H H3-thienyl H 74.294 H H 5-cyanothien-2-yl H 74.295 H H 2-furyl H 74.296 HH 3-furyl H 74.297 H H 1-methyl-1,2,3-triazol-4-yl H 74.298 H H2-methylthiopyrimidin-4-yl H 74.299 H H5-methyl-2-methylthiopyrimidin-4-yl H 74.300 H H pyrazin-2-yl H 74.301 HH 3,6-dimethylpyrazin-2-yl H 74.302 H H 3-cyanopyrazin-2-yl H 74.303 H Hquinolin-2-yl H 74.304 H H 3-ethylquinolin-2-yl H 74.305 H H benzyl H74.306 H H 4-fluorobenzyl H 74.307 H H 4-chlorobenzyl H 74.308 H H4-methylbenzyl H 74.309 H H 2,4-dimethylbenzyl H 74.310 H H2,4,6-trimethylbenzyl H 74.311 H H CH₃ CH₃ 74.312 H H CH₂CH₃ CH₃ 74.313H H n-propyl CH₃ 74.314 H H isopropyl CH₃ 74.315 H H n-butyl CH₃ 74.316H H isobutyl CH₃ 74.317 H H sec-butyl CH₃ 74.318 H H tert-butyl CH₃74.319 H H vinyl CH₃ 74.320 H H ethynyl CH₃ 74.321 H Htrimethylsilylethynyl CH₃ 74.322 H H CH₂OH CH₃ 74.323 H H CH₂OCH₃ CH₃74.324 H H CH₂OCH₂CH₃ CH₃ 74.325 H H CH₂OCH₂OCH₃ CH₃ 74.326 H HCH₂OCH₂OCH₂CH₃ CH₃ 74.327 H H CH₂OCH₂CH₂OCH₃ CH₃ 74.328 H H CHO CH₃74.329 H H COCH₃ CH₃ 74.330 H H CO₂H CH₃ 74.331 H H CO₂CH₃ CH₃ 74.332 HH CO₂CH₂CH₃ CH₃ 74.333 H H CONH₂ CH₃ 74.334 H H CONHCH₃ CH₃ 74.335 H HCONHCH₂CH₃ CH₃ 74.336 H H CON(CH₃)₂ CH₃ 74.337 H H CON(CH₂—CH₃)₂ CH₃74.338 H H CON(CH₃)OCH₃ CH₃ 74.339 H H CH═NOH CH₃ 74.340 H H CH═N—OCH₃CH₃ 74.341 H H CH═N—OCH₂CH₃ CH₃ 74.342 H H C(CH₃)═N—OH CH₃ 74.343 H HC(CH₃)═N—OCH₃ CH₃ 74.344 H H CH₂OC(O)—NHCH₃ CH₃ 74.345 H H CH₂NH₂ CH₃74.346 H H CH₂NHCHO CH₃ 74.347 H H CH₂NHC(O)CH₃ CH₃ 74.348 H HCH₂NHC(O)OCH₃ CH₃ 74.349 H H CH(OH)CH₃ CH₃ 74.350 H H CH(CH₃)OCH₃ CH₃74.351 H H CN CH₃ 74.352 H H CH₂SCH₃ CH₃ 74.353 H H CH₂S(O)CH₃ CH₃74.354 H H CH₂SO₂CH₃ CH₃ 74.355 H H CH₂SCH₂CH₃ CH₃ 74.356 H HCH₂S(O)CH₂CH₃ CH₃ 74.357 H H CH₂SO₂CH₂CH₃ CH₃ 74.358 H H OCH₃ CH₃ 74.359H H OCH₂CH₃ CH₃ 74.360 H H CH(OCH₃)₂ CH₃ 74.361 H H CH(OCH₂CH₃)₂ CH₃74.362 H H cyclopropyl CH₃ 74.363 H H cyclobutyl CH₃ 74.364 H Hcyclopentyl CH₃ 74.365 H H cyclohexyl CH₃ 74.366 H H F CH₃ 74.367 H H ClCH₃ 74.368 H H Br CH₃ 74.369 H H I CH₃ 74.370 H H phenyl CH₃ 74.371 H H2-acetylphenyl CH₃ 74.372 H H 3-acetylphenyl CH₃ 74.373 H H4-acetylphenyl CH₃ 74.374 H H 2-chlorophenyl CH₃ 74.375 H H3-chlorophenyl CH₃ 74.376 H H 4-chlorophenyl CH₃ 74.377 H H2-cyanophenyl CH₃ 74.378 H H 3-cyanophenyl CH₃ 74.379 H H 4-cyanophenylCH₃ 74.380 H H 2-fluorophenyl CH₃ 74.381 H H 3-fluorophenyl CH₃ 74.382 HH 4-fluorophenyl CH₃ 74.383 H H 2-methoxyphenyl CH₃ 74.384 H H3-methoxyphenyl CH₃ 74.385 H H 4-methoxyphenyl CH₃ 74.386 H H2-methylphenyl CH₃ 74.387 H H 3-methylphenyl CH₃ 74.388 H H4-methylphenyl CH₃ 74.389 H H 2-nitrophenyl CH₃ 74.390 H H 3-nitrophenylCH₃ 74.391 H H 4-nitrophenyl CH₃ 74.392 H H 2-thiomethylphenyl CH₃74.393 H H 3-thiomethylphenyl CH₃ 74.394 H H 4-thiomethylphenyl CH₃74.395 H H 2-trifluoromethoxyphenyl CH₃ 74.396 H H3-trifluoromethoxyphenyl CH₃ 74.397 H H 4-trifluoromethoxyphenyl CH₃74.398 H H 2-trifluoromethylphenyl CH₃ 74.399 H H3-trifluoromethylphenyl CH₃ 74.400 H H 4-trifluoromethylphenyl CH₃74.401 H H 2,3-dichlorophenyl CH₃ 74.402 H H 2,4-dichlorophenyl CH₃74.403 H H 2,5-dichlorophenyl CH₃ 74.404 H H 2,6-dichlorophenyl CH₃74.405 H H 3,4-dichlorophenyl CH₃ 74.406 H H 3,5-dichlorophenyl CH₃74.407 H H 2,3-difluorophenyl CH₃ 74.408 H H 2,4-difluorophenyl CH₃74.409 H H 2,5-difluorophenyl CH₃ 74.410 H H 2,6-difluorophenyl CH₃74.411 H H 3,4-difluorophenyl CH₃ 74.412 H H 3,5-difluorophenyl CH₃74.413 H H 2,4,6-trifluorophenyl CH₃ 74.414 H H 2,4-dimethylphenyl CH₃74.415 H H 2,4,6-trimethylphenyl CH₃ 74.416 H H 3,4,5-trimethoxyphenylCH₃ 74.417 H H 2-chloro-3-cyanophenyl CH₃ 74.418 H H2-chloro-4-cyanophenyl CH₃ 74.419 H H 2-chloro-5-cyanophenyl CH₃ 74.420H H 2-chloro-6-cyanophenyl CH₃ 74.421 H H 3-chloro-2-cyanophenyl CH₃74.422 H H 3-chloro-4-cyanophenyl CH₃ 74.423 H H 3-chloro-5-cyanophenylCH₃ 74.424 H H 5-chloro-2-cyanophenyl CH₃ 74.425 H H4-chloro-2-cyanophenyl CH₃ 74.426 H H 4-chloro-3-cyano-phenyl CH₃ 74.427H H 2-chloro-3-fluorophenyl CH₃ 74.428 H H 2-chloro-4-fluorophenyl CH₃74.429 H H 2-chloro-5-fluoro-phenyl CH₃ 74.430 H H2-chloro-6-fluorophenyl CH₃ 74.431 H H 3-chloro-2-fluorophenyl CH₃74.432 H H 3-chloro-4-fluorophenyl CH₃ 74.433 H H3-chloro-5-fluorophenyl CH₃ 74.434 H H 5-chloro-2-fluorophenyl CH₃74.435 H H 4-chloro-2-fluorophenyl CH₃ 74.436 H H4-chloro-3-fluorophenyl CH₃ 74.437 H H 2-chloro-3-methylphenyl CH₃74.438 H H 2-chloro-4-methyl phenyl CH₃ 74.439 H H2-chloro-5-methylphenyl CH₃ 74.440 H H 2-chloro-6-methylphenyl CH₃74.441 H H 3-chloro-2-methylphenyl CH₃ 74.442 H H3-chloro-4-methylphenyl CH₃ 74.443 H H 3-chloro-5-methylphenyl CH₃74.444 H H 5-chloro-2-methylphenyl CH₃ 74.445 H H4-chloro-2-methylphenyl CH₃ 74.446 H H 4-chloro-3-methyl phenyl CH₃74.447 H H 2-cyano-3-fluorophenyl CH₃ 74.448 H H 2-cyano-4-fluorophenylCH₃ 74.449 H H 2-cyano-5-fluorophenyl CH₃ 74.450 H H2-cyano-6-fluorophenyl CH₃ 74.451 H H 3-cyano-2-fluorophenyl CH₃ 74.452H H 3-cyano-4-fluorophenyl CH₃ 74.453 H H 3-cyano-5-fluorophenyl CH₃74.454 H H 5-cyano-2-fluorophenyl CH₃ 74.455 H H 4-cyano-2-fluorophenylCH₃ 74.456 H H 4-cyano-3-fluorophenyl CH₃ 74.457 H H2-fluoro-3-methylphenyl CH₃ 74.458 H H 2-fluoro-4-methylphenyl CH₃74.459 H H 2-fluoro-5-methylphenyl CH₃ 74.460 H H2-fluoro-6-methylphenyl CH₃ 74.461 H H 3-fluoro-2-methylphenyl CH₃74.462 H H 3-fluoro-4-methylphenyl CH₃ 74.463 H H3-fluoro-5-methylphenyl CH₃ 74.464 H H 5-fluoro-2-methylphenyl CH₃74.465 H H 4-fluoro-2-methylphenyl CH₃ 74.466 H H4-fluoro-3-methylphenyl CH₃ 74.467 H H pyridin-2-yl CH₃ 74.468 H Hpyridin-3-yl CH₃ 74.469 H H pyridin-4-yl CH₃ 74.470 H H3-chloropyridin-2-yl CH₃ 74.471 H H 4-chloropyridin-2-yl CH₃ 74.472 H H5-chloropyridin-2-yl CH₃ 74.473 H H 6-chloropyridin-2-yl CH₃ 74.474 H H2-chloropyridin-3-yl CH₃ 74.475 H H 4-chloropyridin-3-yl CH₃ 74.476 H H5-chloropyridin-3-yl CH₃ 74.477 H H 2-chloropyridin-4-yl CH₃ 74.478 H H3-chloropyridin-4-yl CH₃ 74.479 H H 2-chloropyridin-5-yl CH₃ 74.480 H H3-cyanopyridin-2-yl CH₃ 74.481 H H 4-cyanopyridin-2-yl CH₃ 74.482 H H5-cyanopyridin-2-yl CH₃ 74.483 H H 6-cyanopyridin-2-yl CH₃ 74.484 H H2-cyanopyridin-3-yl CH₃ 74.485 H H 4-cyanopyridin-3-yl CH₃ 74.486 H H5-cyanopyridin-3-yl CH₃ 74.487 H H 2-cyanopyridin-5-yl CH₃ 74.488 H H3-fluoropyridin-2-yl CH₃ 74.489 H H 4-fluoropyridin-2-yl CH₃ 74.490 H H5-fluoropyridin-2-yl CH₃ 74.491 H H 6-fluoropyridin-2-yl CH₃ 74.492 H H2-fluoropyridin-3-yl CH₃ 74.493 H H 4-fluoropyridin-3-yl CH₃ 74.494 H H5-fluoropyridin-3-yl CH₃ 74.495 H H 2-fluoropyridin-5-yl CH₃ 74.496 H H3-nitropyridin-2-yl CH₃ 74.497 H H 4-nitropyridin-2-yl CH₃ 74.498 H H5-nitropyridin-2-yl CH₃ 74.499 H H 6-nitropyridin-2-yl CH₃ 74.500 H H2-nitropyridin-3-yl CH₃ 74.501 H H 4-nitropyridin-3-yl CH₃ 74.502 H H5-nitropyridin-3-yl CH₃ 74.503 H H 2-nitropyridin-5-yl CH₃ 74.504 H H3-trifluoromethylpyridin-2-yl CH₃ 74.505 H H4-trifluoromethylpyridin-2-yl CH₃ 74.506 H H5-trifluoromethylpyridin-2-yl CH₃ 74.507 H H6-trifluoromethylpyridin-2-yl CH₃ 74.508 H H2-trifluoromethylpyridin-3-yl CH₃ 74.509 H H4-trifluoromethylpyridin-3-yl CH₃ 74.510 H H5-trifluoromethylpyridin-3-yl CH₃ 74.511 H H2-trifluoromethylpyridin-5-yl CH₃ 74.512 H H2,6-bis(trifluoromethyl)pyridin-3-yl CH₃ 74.513 H H2,6-bis(trifluoromethyl)pyridin-4-yl CH₃ 74.514 H H3,5-bis(trifluoromethyl)pyridin-2-yl CH₃ 74.515 H H 2-thienyl CH₃ 74.516H H 3-thienyl CH₃ 74.517 H H 5-cyanothien-2-yl CH₃ 74.518 H H 2-furylCH₃ 74.519 H H 3-furyl CH₃ 74.520 H H 1-methyl-1,2,3-triazol-4-yl CH₃74.521 H H 2-methylthiopyrimidin-4-yl CH₃ 74.522 H H5-methyl-2-methylthiopyrimidin-4-yl CH₃ 74.523 H H pyrazin-2-yl CH₃74.524 H H 3,6-dimethylpyrazin-2-yl CH₃ 74.525 H H 3-cyanopyrazin-2-ylCH₃ 74.526 H H quinolin-2-yl CH₃ 74.527 H H 3-ethylquinolin-2-yl CH₃74.528 H H benzyl CH₃ 74.529 H H 4-fluorobenzyl CH₃ 74.530 H H4-chlorobenzyl CH₃ 74.531 H H 4-methylbenzyl CH₃ 74.532 H H2,4-dimethylbenzyl CH₃ 74.533 H H 2,4,6-trimethylbenzyl CH₃ 74.534 CH₃ HCH₃ H 74.535 CH₃ H CH₂CH₃ H 74.536 CH₃ H n-propyl H 74.537 CH₃ Hisopropyl H 74.538 CH₃ H n-butyl H 74.539 CH₃ H isobutyl H 74.540 CH₃ Hsec-butyl H 74.541 CH₃ H tert-butyl H 74.542 CH₃ H vinyl H 74.543 CH₃ Hethynyl H 74.544 CH₃ H trimethylsilylethynyl H 74.545 CH₃ H CH₂OH H74.546 CH₃ H CH₂OCH₃ H 74.547 CH₃ H CH₂OCH₂CH₃ H 74.548 CH₃ HCH₂OCH₂OCH₃ H 74.549 CH₃ H CH₂OCH₂OCH₂CH₃ H 74.550 CH₃ H CH₂OCH₂CH₂OCH₃H 74.551 CH₃ H CHO H 74.552 CH₃ H COCH₃ H 74.553 CH₃ H CO₂H H 74.554 CH₃H CO₂CH₃ H 74.555 CH₃ H CO₂CH₂CH₃ H 74.556 CH₃ H CONH₂ H 74.557 CH₃ HCONHCH₃ H 74.558 CH₃ H CONHCH₂CH₃ H 74.559 CH₃ H CON(CH₃)₂ H 74.560 CH₃H CON(CH₂—CH₃)₂ H 74.561 CH₃ H CON(CH₃)OCH₃ H 74.562 CH₃ H CH═NOH H74.563 CH₃ H CH═N—OCH₃ H 74.564 CH₃ H CH═N—OCH₂CH₃ H 74.565 CH₃ HC(CH₃)═N—OH H 74.566 CH₃ H C(CH₃)═N—OCH₃ H 74.567 CH₃ H CH₂OC(O)—NHCH₃ H74.568 CH₃ H CH₂NH₂ H 74.569 CH₃ H CH₂NHCHO H 74.570 CH₃ H CH₂NHC(O)CH₃H 74.571 CH₃ H CH₂NHC(O)OCH₃ H 74.572 CH₃ H CH(OH)CH₃ H 74.573 CH₃ HCH(CH₃)OCH₃ H 74.574 CH₃ H CN H 74.575 CH₃ H CH₂SCH₃ H 74.576 CH₃ HCH₂S(O)CH₃ H 74.577 CH₃ H CH₂SO₂CH₃ H 74.578 CH₃ H CH₂SCH₂CH₃ H 74.579CH₃ H CH₂S(O)CH₂CH₃ H 74.580 CH₃ H CH₂SO₂CH₂CH₃ H 74.581 CH₃ H OCH₃ H74.582 CH₃ H OCH₂CH₃ H 74.583 CH₃ H CH(OCH₃)₂ H 74.584 CH₃ HCH(OCH₂CH₃)₂ H 74.585 CH₃ H cyclopropyl H 74.586 CH₃ H cyclobutyl H74.587 CH₃ H cyclopentyl H 74.588 CH₃ H cyclohexyl H 74.589 CH₃ H F H74.590 CH₃ H Cl H 74.591 CH₃ H Br H 74.592 CH₃ H I H 74.593 CH₃ H phenylH 74.594 CH₃ H 2-acetylphenyl H 74.595 CH₃ H 3-acetylphenyl H 74.596 CH₃H 4-acetylphenyl H 74.597 CH₃ H 2-chlorophenyl H 74.598 CH₃ H3-chlorophenyl H 74.599 CH₃ H 4-chlorophenyl H 74.600 CH₃ H2-cyanophenyl H 74.601 CH₃ H 3-cyanophenyl H 74.602 CH₃ H 4-cyanophenylH 74.603 CH₃ H 2-fluorophenyl H 74.604 CH₃ H 3-fluorophenyl H 74.605 CH₃H 4-fluorophenyl H 74.606 CH₃ H 2-methoxyphenyl H 74.607 CH₃ H3-methoxyphenyl H 74.608 CH₃ H 4-methoxyphenyl H 74.609 CH₃ H2-methylphenyl H 74.610 CH₃ H 3-methylphenyl H 74.611 CH₃ H4-methylphenyl H 74.612 CH₃ H 2-nitrophenyl H 74.613 CH₃ H 3-nitrophenylH 74.614 CH₃ H 4-nitrophenyl H 74.615 CH₃ H 2-thiomethylphenyl H 74.616CH₃ H 3-thiomethylphenyl H 74.617 CH₃ H 4-thiomethylphenyl H 74.618 CH₃H 2-trifluoromethoxyphenyl H 74.619 CH₃ H 3-trifluoromethoxyphenyl H74.620 CH₃ H 4-trifluoromethoxyphenyl H 74.621 CH₃ H2-trifluoromethylphenyl H 74.622 CH₃ H 3-trifluoromethylphenyl H 74.623CH₃ H 4-trifluoromethylphenyl H 74.624 CH₃ H 2,3-dichlorophenyl H 74.625CH₃ H 2,4-dichlorophenyl H 74.626 CH₃ H 2,5-dichlorophenyl H 74.627 CH₃H 2,6-dichlorophenyl H 74.628 CH₃ H 3,4-dichlorophenyl H 74.629 CH₃ H3,5-dichlorophenyl H 74.630 CH₃ H 2,3-difluorophenyl H 74.631 CH₃ H2,4-difluorophenyl H 74.632 CH₃ H 2,5-difluorophenyl H 74.633 CH₃ H2,6-difluorophenyl H 74.634 CH₃ H 3,4-difluorophenyl H 74.635 CH₃ H3,5-difluorophenyl H 74.636 CH₃ H 2,4,6-trifluorophenyl H 74.637 CH₃ H2,4-dimethylphenyl H 74.638 CH₃ H 2,4,6-trimethylphenyl H 74.639 CH₃ H3,4,5-trimethoxyphenyl H 74.640 CH₃ H 2-chloro-3-cyanophenyl H 74.641CH₃ H 2-chloro-4-cyanophenyl H 74.642 CH₃ H 2-chloro-5-cyanophenyl H74.643 CH₃ H 2-chloro-6-cyanophenyl H 74.644 CH₃ H3-chloro-2-cyanophenyl H 74.645 CH₃ H 3-chloro-4-cyanophenyl H 74.646CH₃ H 3-chloro-5-cyanophenyl H 74.647 CH₃ H 5-chloro-2-cyanophenyl H74.648 CH₃ H 4-chloro-2-cyanophenyl H 74.649 CH₃ H4-chloro-3-cyanophenyl H 74.650 CH₃ H 2-chloro-3-fluorophenyl H 74.651CH₃ H 2-chloro-4-fluorophenyl H 74.652 CH₃ H 2-chloro-5-fluorophenyl H74.653 CH₃ H 2-chloro-6-fluorophenyl H 74.654 CH₃ H3-chloro-2-fluorophenyl H 74.655 CH₃ H 3-chloro-4-fluorophenyl H 74.656CH₃ H 3-chloro-5-fluorophenyl H 74.657 CH₃ H 5-chloro-2-fluorophenyl H74.658 CH₃ H 4-chloro-2-fluorophenyl H 74.659 CH₃ H4-chloro-3-fluorophenyl H 74.660 CH₃ H 2-chloro-3-methylphenyl H 74.661CH₃ H 2-chloro-4-methylphenyl H 74.662 CH₃ H 2-chloro-5-methylphenyl H74.663 CH₃ H 2-chloro-6-methylphenyl H 74.664 CH₃ H3-chloro-2-methylphenyl H 74.665 CH₃ H 3-chloro-4-methylphenyl H 74.666CH₃ H 3-chloro-5-methylphenyl H 74.667 CH₃ H 5-chloro-2-methylphenyl H74.668 CH₃ H 4-chloro-2-methylphenyl H 74.669 CH₃ H4-chloro-3-methylphenyl H 74.670 CH₃ H 2-cyano-3-fluorophenyl H 74.671CH₃ H 2-cyano-4-fluorophenyl H 74.672 CH₃ H 2-cyano-5-fluorophenyl H74.673 CH₃ H 2-cyano-6-fluorophenyl H 74.674 CH₃ H3-cyano-2-fluorophenyl H 74.675 CH₃ H 3-cyano-4-fluorophenyl H 74.676CH₃ H 3-cyano-5-fluorophenyl H 74.677 CH₃ H 5-cyano-2-fluorophenyl H74.678 CH₃ H 4-cyano-2-fluorophenyl H 74.679 CH₃ H4-cyano-3-fluorophenyl H 74.680 CH₃ H 2-fluoro-3-methylphenyl H 74.681CH₃ H 2-fluoro-4-methylphenyl H 74.682 CH₃ H 2-fluoro-5-methylphenyl H74.683 CH₃ H 2-fluoro-6-methylphenyl H 74.684 CH₃ H3-fluoro-2-methylphenyl H 74.685 CH₃ H 3-fluoro-4-methylphenyl H 74.686CH₃ H 3-fluoro-5-methylphenyl H 74.687 CH₃ H 5-fluoro-2-methylphenyl H74.688 CH₃ H 4-fluoro-2-methylphenyl H 74.689 CH₃ H4-fluoro-3-methylphenyl H 74.690 CH₃ H pyridin-2-yl H 74.691 CH₃ Hpyridin-3-yl H 74.692 CH₃ H pyridin-4-yl H 74.693 CH₃ H3-chloropyridin-2-yl H 74.694 CH₃ H 4-chloropyridin-2-yl H 74.695 CH₃ H5-chloropyridin-2-yl H 74.696 CH₃ H 6-chloropyridin-2-yl H 74.697 CH₃ H2-chloropyridin-3-yl H 74.698 CH₃ H 4-chloropyridin-3-yl H 74.699 CH₃ H5-chloropyridin-3-yl H 74.700 CH₃ H 2-chloropyridin-4-yl H 74.701 CH₃ H3-chloropyridin-4-yl H 74.702 CH₃ H 2-chloropyridin-5-yl H 74.703 CH₃ H3-cyanopyridin-2-yl H 74.704 CH₃ H 4-cyanopyridin-2-yl H 74.705 CH₃ H5-cyanopyridin-2-yl H 74.706 CH₃ H 6-cyanopyridin-2-yl H 74.707 CH₃ H2-cyanopyridin-3-yl H 74.708 CH₃ H 4-cyanopyridin-3-yl H 74.709 CH₃ H5-cyanopyridin-3-yl H 74.710 CH₃ H 2-cyanopyridin-5-yl H 74.711 CH₃ H3-fluoropyridin-2-yl H 74.712 CH₃ H 4-fluoropyridin-2-yl H 74.713 CH₃ H5-fluoropyridin-2-yl H 74.714 CH₃ H 6-fluoropyridin-2-yl H 74.715 CH₃ H2-fluoropyridin-3-yl H 74.716 CH₃ H 4-fluoropyridin-3-yl H 74.717 CH₃ H5-fluoropyridin-3-yl H 74.718 CH₃ H 2-fluoropyridin-5-yl H 74.719 CH₃ H3-nitropyridin-2-yl H 74.720 CH₃ H 4-nitropyridin-2-yl H 74.721 CH₃ H5-nitropyridin-2-yl H 74.722 CH₃ H 6-nitropyridin-2-yl H 74.723 CH₃ H2-nitropyridin-3-yl H 74.724 CH₃ H 4-nitropyridin-3-yl H 74.725 CH₃ H5-nitropyridin-3-yl H 74.726 CH₃ H 2-nitropyridin-5-yl H 74.727 CH₃ H3-trifluoromethylpyridin-2-yl H 74.728 CH₃ H4-trifluoromethylpyridin-2-yl H 74.729 CH₃ H5-trifluoromethylpyridin-2-yl H 74.730 CH₃ H6-trifluoromethylpyridin-2-yl H 74.731 CH₃ H2-trifluoromethylpyridin-3-yl H 74.732 CH₃ H4-trifluoromethylpyridin-3-yl H 74.733 CH₃ H5-trifluoromethylpyridin-3-yl H 74.734 CH₃ H2-trifluoromethylpyridin-5-yl H 74.735 CH₃ H2,6-bis(trifluoromethyl)pyridin-3-yl H 74.736 CH₃ H2,6-bis(trifluoromethyl)pyridin-4-yl H 74.737 CH₃ H3,5-bis(trifluoromethyl)pyridin-2-yl H 74.738 CH₃ H 2-thienyl H 74.739CH₃ H 3-thienyl H 74.740 CH₃ H 5-cyanothien-2-yl H 74.741 CH₃ H 2-furylH 74.742 CH₃ H 3-furyl H 74.743 CH₃ H 1-methyl-1,2,3-triazol-4-yl H74.744 CH₃ H 2-methylthiopyrimidin-4-yl H 74.745 CH₃ H5-methyl-2-methylthiopyrimidin-4-yl H 74.746 CH₃ H pyrazin-2-yl H 74.747CH₃ H 3,6-dimethylpyrazin-2-yl H 74.748 CH₃ H 3-cyanopyrazin-2-yl H74.749 CH₃ H quinolin-2-yl H 74.750 CH₃ H 3-ethylquinolin-2-yl H 74.751CH₃ H benzyl H 74.752 CH₃ H 4-fluorobenzyl H 74.753 CH₃ H 4-chlorobenzylH 74.754 CH₃ H 4-methylbenzyl H 74.755 CH₃ H 2,4-dimethylbenzyl H 74.756CH₃ H 2,4,6-trimethylbenzyl H 74.757 CH₃ H H CH₃ 74.758 CH₃ H CH₃ CH₃74.759 CH₃ H CH₂CH₃ CH₃ 74.760 CH₃ H n-propyl CH₃ 74.761 CH₃ H isopropylCH₃ 74.762 CH₃ H n-butyl CH₃ 74.763 CH₃ H isobutyl CH₃ 74.764 CH₃ Hsec-butyl CH₃ 74.765 CH₃ H tert-butyl CH₃ 74.766 CH₃ H vinyl CH₃ 74.767CH₃ H ethynyl CH₃ 74.768 CH₃ H trimethylsilylethynyl CH₃ 74.769 CH₃ HCH₂OH CH₃ 74.770 CH₃ H CH₂OCH₃ CH₃ 74.771 CH₃ H CH₂OCH₂CH₃ CH₃ 74.772CH₃ H CH₂OCH₂OCH₃ CH₃ 74.773 CH₃ H CH₂OCH₂OCH₂CH₃ CH₃ 74.774 CH₃ HCH₂OCH₂CH₂OCH₃ CH₃ 74.775 CH₃ H CHO CH₃ 74.776 CH₃ H COCH₃ CH₃ 74.777CH₃ H CO₂H CH₃ 74.778 CH₃ H CO₂CH₃ CH₃ 74.779 CH₃ H CO₂CH₂CH₃ CH₃ 74.780CH₃ H CONH₂ CH₃ 74.781 CH₃ H CONHCH₃ CH₃ 74.782 CH₃ H CONHCH₂CH₃ CH₃74.783 CH₃ H CON(CH₃)₂ CH₃ 74.784 CH₃ H CON(CH₂—CH₃)₂ CH₃ 74.785 CH₃ HCON(CH₃)OCH₃ CH₃ 74.786 CH₃ H CH═NOH CH₃ 74.787 CH₃ H CH═N—OCH₃ CH₃74.788 CH₃ H CH═N—OCH₂CH₃ CH₃ 74.789 CH₃ H C(CH₃)═N—OH CH₃ 74.790 CH₃ HC(CH₃)═N—OCH₃ CH₃ 74.791 CH₃ H CH₂OC(O)—NHCH₃ CH₃ 74.792 CH₃ H CH₂NH₂CH₃ 74.793 CH₃ H CH₂NHCHO CH₃ 74.794 CH₃ H CH₂NHC(O)CH₃ CH₃ 74.795 CH₃ HCH₂NHC(O)OCH₃ CH₃ 74.796 CH₃ H CH(OH)CH₃ CH₃ 74.797 CH₃ H CH(CH₃)OCH₃CH₃ 74.798 CH₃ H CN CH₃ 74.799 CH₃ H CH₂SCH₃ CH₃ 74.800 CH₃ H CH₂S(O)CH₃CH₃ 74.801 CH₃ H CH₂SO₂CH₃ CH₃ 74.802 CH₃ H CH₂SCH₂CH₃ CH₃ 74.803 CH₃ HCH₂S(O)CH₂CH₃ CH₃ 74.804 CH₃ H CH₂SO₂CH₂CH₃ CH₃ 74.805 CH₃ H OCH₃ CH₃74.806 CH₃ H OCH₂CH₃ CH₃ 74.807 CH₃ H CH(OCH₃)₂ CH₃ 74.808 CH₃ HCH(OCH₂CH₃)₂ CH₃ 74.809 CH₃ H cyclopropyl CH₃ 74.810 CH₃ H cyclobutylCH₃ 74.811 CH₃ H cyclopentyl CH₃ 74.812 CH₃ H cyclohexyl CH₃ 74.813 CH₃H F CH₃ 74.814 CH₃ H Cl CH₃ 74.815 CH₃ H Br CH₃ 74.816 CH₃ H I CH₃74.817 CH₃ H phenyl CH₃ 74.818 CH₃ H 2-acetylphenyl CH₃ 74.819 CH₃ H3-acetylphenyl CH₃ 74.820 CH₃ H 4-acetylphenyl CH₃ 74.821 CH₃ H2-chlorophenyl CH₃ 74.822 CH₃ H 3-chlorophenyl CH₃ 74.823 CH₃ H4-chlorophenyl CH₃ 74.824 CH₃ H 2-cyanophenyl CH₃ 74.825 CH₃ H3-cyanophenyl CH₃ 74.826 CH₃ H 4-cyanophenyl CH₃ 74.827 CH₃ H2-fluorophenyl CH₃ 74.828 CH₃ H 3-fluorophenyl CH₃ 74.829 CH₃ H4-fluorophenyl CH₃ 74.830 CH₃ H 2-methoxyphenyl CH₃ 74.831 CH₃ H3-methoxyphenyl CH₃ 74.832 CH₃ H 4-methoxyphenyl CH₃ 74.833 CH₃ H2-methylphenyl CH₃ 74.834 CH₃ H 3-methylphenyl CH₃ 74.835 CH₃ H4-methylphenyl CH₃ 74.836 CH₃ H 2-nitrophenyl CH₃ 74.837 CH₃ H3-nitrophenyl CH₃ 74.838 CH₃ H 4-nitrophenyl CH₃ 74.839 CH₃ H2-thiomethylphenyl CH₃ 74.840 CH₃ H 3-thiomethylphenyl CH₃ 74.841 CH₃ H4-thiomethylphenyl CH₃ 74.842 CH₃ H 2-trifluoromethoxyphenyl CH₃ 74.843CH₃ H 3-trifluoromethoxyphenyl CH₃ 74.844 CH₃ H 4-trifluoromethoxyphenylCH₃ 74.845 CH₃ H 2-trifluoromethylphenyl CH₃ 74.846 CH₃ H3-trifluoromethylphenyl CH₃ 74.847 CH₃ H 4-trifluoromethylphenyl CH₃74.848 CH₃ H 2,3-dichlorophenyl CH₃ 74.849 CH₃ H 2,4-dichlorophenyl CH₃74.850 CH₃ H 2,5-dichlorophenyl CH₃ 74.851 CH₃ H 2,6-dichlorophenyl CH₃74.852 CH₃ H 3,4-dichlorophenyl CH₃ 74.853 CH₃ H 3,5-dichlorophenyl CH₃74.854 CH₃ H 2,3-difluorophenyl CH₃ 74.855 CH₃ H 2,4-difluorophenyl CH₃74.856 CH₃ H 2,5-difluorophenyl CH₃ 74.857 CH₃ H 2,6-difluorophenyl CH₃74.858 CH₃ H 3,4-difluorophenyl CH₃ 74.859 CH₃ H 3,5-difluorophenyl CH₃74.860 CH₃ H 2,4,6-trifluorophenyl CH₃ 74.861 CH₃ H 2,4-dimethylphenylCH₃ 74.862 CH₃ H 2,4,6-trimethylphenyl CH₃ 74.863 CH₃ H3,4,5-trimethoxyphenyl CH₃ 74.864 CH₃ H 2-chloro-3-cyanophenyl CH₃74.865 CH₃ H 2-chloro-4-cyanophenyl CH₃ 74.866 CH₃ H2-chloro-5-cyanophenyl CH₃ 74.867 CH₃ H 2-chloro-6-cyanophenyl CH₃74.868 CH₃ H 3-chloro-2-cyanophenyl CH₃ 74.869 CH₃ H3-chloro-4-cyanophenyl CH₃ 74.870 CH₃ H 3-chloro-5-cyanophenyl CH₃74.871 CH₃ H 5-chloro-2-cyanophenyl CH₃ 74.872 CH₃ H4-chloro-2-cyanophenyl CH₃ 74.873 CH₃ H 4-chloro-3-cyanophenyl CH₃74.874 CH₃ H 2-chloro-3-fluorophenyl CH₃ 74.875 CH₃ H2-chloro-4-fluorophenyl CH₃ 74.876 CH₃ H 2-chloro-5-fluorophenyl CH₃74.877 CH₃ H 2-chloro-6-fluorophenyl CH₃ 74.878 CH₃ H3-chloro-2-fluorophenyl CH₃ 74.879 CH₃ H 3-chloro-4-fluorophenyl CH₃74.880 CH₃ H 3-chloro-5-fluorophenyl CH₃ 74.881 CH₃ H5-chloro-2-fluorophenyl CH₃ 74.882 CH₃ H 4-chloro-2-fluorophenyl CH₃74.883 CH₃ H 4-chloro-3-fluorophenyl CH₃ 74.884 CH₃ H2-chloro-3-methylphenyl CH₃ 74.885 CH₃ H 2-chloro-4-methylphenyl CH₃74.886 CH₃ H 2-chloro-5-methylphenyl CH₃ 74.887 CH₃ H2-chloro-6-methylphenyl CH₃ 74.888 CH₃ H 3-chloro-2-methylphenyl CH₃74.889 CH₃ H 3-chloro-4-methylphenyl CH₃ 74.890 CH₃ H3-chloro-5-methylphenyl CH₃ 74.891 CH₃ H 5-chloro-2-methylphenyl CH₃74.892 CH₃ H 4-chloro-2-methylphenyl CH₃ 74.893 CH₃ H4-chloro-3-methylphenyl CH₃ 74.894 CH₃ H 2-cyano-3-fluorophenyl CH₃74.895 CH₃ H 2-cyano-4-fluorophenyl CH₃ 74.896 CH₃ H2-cyano-5-fluorophenyl CH₃ 74.897 CH₃ H 2-cyano-6-fluorophenyl CH₃74.898 CH₃ H 3-cyano-2-fluorophenyl CH₃ 74.899 CH₃ H3-cyano-4-fluorophenyl CH₃ 74.901 CH₃ H 3-cyano-5-fluorophenyl CH₃74.902 CH₃ H 5-cyano-2-fluorophenyl CH₃ 74.903 CH₃ H4-cyano-2-fluorophenyl CH₃ 74.904 CH₃ H 4-cyano-3-fluorophenyl CH₃74.905 CH₃ H 2-fluoro-3-methylphenyl CH₃ 74.906 CH₃ H2-fluoro-4-methylphenyl CH₃ 74.907 CH₃ H 2-fluoro-5-methylphenyl CH₃74.908 CH₃ H 2-fluoro-6-methylphenyl CH₃ 74.909 CH₃ H3-fluoro-2-methylphenyl CH₃ 74.910 CH₃ H 3-fluoro-4-methylphenyl CH₃74.911 CH₃ H 3-fluoro-5-methylphenyl CH₃ 74.912 CH₃ H5-fluoro-2-methylphenyl CH₃ 74.913 CH₃ H 4-fluoro-2-methylphenyl CH₃74.914 CH₃ H 4-fluoro-3-methylphenyl CH₃ 74.915 CH₃ H pyridin-2-yl CH₃74.916 CH₃ H pyridin-3-yl CH₃ 74.917 CH₃ H pyridin-4-yl CH₃ 74.918 CH₃ H3-chloropyridin-2-yl CH₃ 74.919 CH₃ H 4-chloropyridin-2-yl CH₃ 74.920CH₃ H 5-chloropyridin-2-yl CH₃ 74.921 CH₃ H 6-chloropyridin-2-yl CH₃74.922 CH₃ H 2-chloropyridin-3-yl CH₃ 74.923 CH₃ H 4-chloropyridin-3-ylCH₃ 74.924 CH₃ H 5-chloropyridin-3-yl CH₃ 74.925 CH₃ H2-chloropyridin-4-yl CH₃ 74.926 CH₃ H 3-chloropyridin-4-yl CH₃ 74.927CH₃ H 2-chloropyridin-5-yl CH₃ 74.928 CH₃ H 3-cyanopyridin-2-yl CH₃74.929 CH₃ H 4-cyanopyridin-2-yl CH₃ 74.930 CH₃ H 5-cyanopyridin-2-ylCH₃ 74.931 CH₃ H 6-cyanopyridin-2-yl CH₃ 74.932 CH₃ H2-cyanopyridin-3-yl CH₃ 74.933 CH₃ H 4-cyanopyridin-3-yl CH₃ 74.934 CH₃H 5-cyanopyridin-3-yl CH₃ 74.935 CH₃ H 2-cyanopyridin-5-yl CH₃ 74.936CH₃ H 3-fluoropyridin-2-yl CH₃ 74.937 CH₃ H 4-fluoropyridin-2-yl CH₃74.938 CH₃ H 5-fluoropyridin-2-yl CH₃ 74.939 CH₃ H 6-fluoropyridin-2-ylCH₃ 74.940 CH₃ H 2-fluoropyridin-3-yl CH₃ 74.941 CH₃ H4-fluoropyridin-3-yl CH₃ 74.942 CH₃ H 5-fluoropyridin-3-yl CH₃ 74.943CH₃ H 2-fluoropyridin-5-yl CH₃ 74.944 CH₃ H 3-nitropyridin-2-yl CH₃74.945 CH₃ H 4-nitropyridin-2-yl CH₃ 74.946 CH₃ H 5-nitropyridin-2-ylCH₃ 74.947 CH₃ H 6-nitropyridin-2-yl CH₃ 74.948 CH₃ H2-nitropyridin-3-yl CH₃ 74.949 CH₃ H 4-nitropyridin-3-yl CH₃ 74.950 CH₃H 5-nitropyridin-3-yl CH₃ 74.951 CH₃ H 2-nitropyridin-5-yl CH₃ 74.952CH₃ H 3-trifluoromethylpyridin-2-yl CH₃ 74.953 CH₃ H4-trifluoromethylpyridin-2-yl CH₃ 74.954 CH₃ H5-trifluoromethylpyridin-2-yl CH₃ 74.955 CH₃ H6-trifluoromethylpyridin-2-yl CH₃ 74.956 CH₃ H2-trifluoromethylpyridin-3-yl CH₃ 74.957 CH₃ H4-trifluoromethylpyridin-3-yl CH₃ 74.958 CH₃ H5-trifluoromethylpyridin-3-yl CH₃ 74.959 CH₃ H2-trifluoromethylpyridin-5-yl CH₃ 74.960 CH₃ H2,6-bis(trifluoromethyl)pyridin-3-yl CH₃ 74.961 CH₃ H2,6-bis(trifluoromethyl)pyridin-4-yl CH₃ 74.962 CH₃ H3,5-bis(trifluoromethyl)pyridin-2-yl CH₃ 74.963 CH₃ H 2-thienyl CH₃74.964 CH₃ H 3-thienyl CH₃ 74.965 CH₃ H 5-cyanothien-2-yl CH₃ 74.966 CH₃H 2-furyl CH₃ 74.967 CH₃ H 3-furyl CH₃ 74.968 CH₃ H1-methyl-1,2,3-triazol-4-yl CH₃ 74.969 CH₃ H 2-methylthiopyrimidin-4-ylCH₃ 74.970 CH₃ H 5-methyl-2-methylthiopyrimidin-4-yl CH₃ 74.971 CH₃ Hpyrazin-2-yl CH₃ 74.972 CH₃ H 3,6-dimethylpyrazin-2-yl CH₃ 74.973 CH₃ H3-cyanopyrazin-2-yl CH₃ 74.974 CH₃ H quinolin-2-yl CH₃ 74.975 CH₃ H3-ethylquinolin-2-yl CH₃ 74.976 CH₃ H benzyl CH₃ 74.977 CH₃ H4-fluorobenzyl CH₃ 74.978 CH₃ H 4-chlorobenzyl CH₃ 74.979 CH₃ H4-methylbenzyl CH₃ 74.980 CH₃ H 2,4-dimethylbenzyl CH₃ 74.981 CH₃ H2,4,6-trimethylbenzyl CH₃ 74.982 CH₃ H H CH₂OH 74.983 CH₃ H H CH₂OCH₃74.984 CH₃ H H CH₂OCH₂CH₃ 74.985 CH₃ H H CHO 74.986 CH₃ H H COCH₃ 74.987CH₃ H H CO₂H 74.988 CH₃ H H CO₂CH₃ 74.989 CH₃ H H CO₂CH₂CH₃ 74.990 CH₃ HH CONH₂ 74.991 CH₃ H H CONHCH₃ 74.992 CH₃ H H CONHCH₂CH₃ 74.993 CH₃ H HCON(CH₃)₂ 74.994 CH₃ H H CON—(CH₂CH₃)₂ 74.995 CH₃ H H CON(CH₃)O—CH₃74.996 CH₃ H H CH═NOH 74.997 CH₃ H H CH═NOCH₃ 74.998 CH₃ H HCH═NOCH₂—CH₃ 74.999 CH₃ H H C(CH₃)═NOH 74.1000 CH₃ H H C(CH₃)═NO—CH₃74.1001 CH₃ H H CH₂OC(O)NH—CH₃ 74.1002 CH₃ H H CH₂NH₂ 74.1003 CH₃ H HCH₂NHCHO 74.1004 CH₃ H H CH₂NHC(O)—CH₃ 74.1005 CH₃ H H CH₂NHC(O)OCH₃74.1006 CH₃ H H NHCO₂CH₃ 74.1007 CH₃ H H NHCO₂—C(CH₃)₃ 74.1008 CH₃ H HCH(OH)CH₃ 74.1009 CH₃ H H CH(CH₃)OCH₃ 74.1010 CH₃ H H CN 74.1011 CH₃ H HCH₂SCH₃ 74.1012 CH₃ H H CH₂S(O)CH₃ 74.1013 CH₃ H H CH₂SO₂CH₃ 74.1014 CH₃H H CH₂SCH₂CH₃ 74.1015 CH₃ H H CH₂S(O)CH₂—CH₃ 74.1016 CH₃ H HCH₂SO₂CH₂—CH₃ 74.1017 CH₃ H H OCH₃ 74.1018 CH₃ H H OCH₂CH₃ 74.1019 CH₃ HH CH(OCH₃)₂ 74.1020 CH₃ H H CH—(OCH₂CH₃)₂ 74.1021 CH₃ H H CH₂CH₃ 74.1022CH₃ H H CH₂CH₂CH₃ 74.1023 CH₃ H H CH(CH₃)₂ 74.1024 CH₃ H H C(CH₃)₃74.1025 CH₃ H H CH₂CH(CH₃)₂ 74.1026 CH₃ H H CH₂C(CH₃)₃ 74.1027 CH₃ H HCH₂CN 74.1028 CH₃ H H cyclopropyl 74.1029 CH₃ H H cyclobutyl 74.1030 CH₃H H cyclopentyl 74.1031 CH₃ H H cyclohexyl 74.1032 CH₃ H HCH₂-cyclopropyl 74.1033 CH₃ H H benzyl 74.1034 CH₃ H H CH₂CF₃

Table 75 covers compounds of formula (AH), wherein R¹ is ethyl, R² andR⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 76 covers compounds of formula (AH), wherein Wand R⁴ are ethyl, R²is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 77 covers compounds of formula (AH), wherein R¹, R² and R⁴ areethyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 78 covers compounds of formula (AH), wherein R¹ and R² are methyl,R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are as definedin Table 74.

Table 79 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 80 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 81 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 82 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 83 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is ethynyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 84 covers compounds of formula (AH), wherein R¹ and R² are methyl,R⁴ is vinyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 85 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 86 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 87 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 88 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 89 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 90 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is ethynyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 91 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethyl, R⁴ is vinyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Table 92 covers compounds of formula (AH), wherein R¹ is ethynyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 93 covers compounds of formula (AH), wherein R¹ is ethynyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 94 covers compounds of formula (AH), wherein R¹ is ethynyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 95 covers compounds of formula (AH), wherein R¹ is ethynyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 96 covers compounds of formula (AH), wherein R¹ is ethynyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 97 covers compounds of formula (AH), wherein R¹ and R⁴ areethynyl, R² is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 98 covers compounds of formula (AH), wherein R¹ is vinyl, R² ismethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 99 covers compounds of formula (AH), wherein R¹ is vinyl, R² ismethyl, R⁴ is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 100 covers compounds of formula (AH), wherein R¹ is vinyl, R² ismethyl, R⁴ is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 101 covers compounds of formula (AH), wherein R¹ is vinyl, R² ismethyl, R⁴ is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 102 covers compounds of formula (AH), wherein R¹ is vinyl, R² ismethyl, R⁴ is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 103 covers compounds of formula (AH), wherein R¹ and R⁴ are vinyl,R² is methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 104 covers compounds of formula (AH), wherein R¹ is methyl, R²,R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are as definedin Table 74.

Table 105 covers compounds of formula (AH), wherein R¹ is methyl, R² ismethoxy, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 106 covers compounds of formula (AH), wherein R¹ is methyl, R² istrifluoromethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Table 107 covers compounds of formula (AH), wherein R¹ is methyl, R² isethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 108 covers compounds of formula (AH), wherein R¹ is methyl, R² isethynyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 109 covers compounds of formula (AH), wherein R¹ is methyl, R² isvinyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 110 covers compounds of formula (AH), wherein R¹ is methyl, R² ischlorine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 111 covers compounds of formula (AH), wherein R¹ is methyl, R² isbromine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 112 covers compounds of formula (AH), wherein R¹ is methyl, R² isiodine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 113 covers compounds of formula (AH), wherein R¹ is ethyl, R², R³,R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are as defined inTable 74.

Table 114 covers compounds of formula (AH), wherein R¹ is ethyl, R² ismethoxy, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 115 covers compounds of formula (AH), wherein R¹ and R² are ethyl,R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are as definedin Table 74.

Table 116 covers compounds of formula (AH), wherein R¹ is ethyl, R² istrifluoromethyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Table 117 covers compounds of formula (AH), wherein R¹ is ethyl, R² isethynyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 118 covers compounds of formula (AH), wherein R¹ is ethyl, R² isvinyl, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 119 covers compounds of formula (AH), wherein R¹ is ethyl, R² ischlorine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 120 covers compounds of formula (AH), wherein R¹ is ethyl, R² isbromine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 121 covers compounds of formula (AH), wherein R¹ is ethyl, R² isiodine, R³, R⁴, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 122 covers compounds of formula (AH), wherein R¹ and R⁴ aremethyl, R² is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 123 covers compounds of formula (AH), wherein R¹ and R⁴ aremethyl, R² is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 124 covers compounds of formula (AH), wherein R¹ and R⁴ aremethyl, R² is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 125 covers compounds of formula (AH), wherein R¹ is methyl, R² ischlorine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 126 covers compounds of formula (AH), wherein R¹ is methyl, R² isbromine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 127 covers compounds of formula (AH), wherein R¹ is methyl, R² isiodine, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶, R⁸,R⁹, and R¹¹ are as defined in Table 74.

Table 128 covers compounds of formula (AH), wherein R¹ and R⁴ are ethyl,R² is chlorine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 129 covers compounds of formula (AH), wherein R¹ and R⁴ aremethyl, R² is bromine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 130 covers compounds of formula (AH), wherein R¹ and R⁴ are ethyl,R² is iodine, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are asdefined in Table 74.

Table 131 covers compounds of formula (AH), wherein R¹ is methyl, R² ischlorine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 132 covers compounds of formula (AH), wherein R¹ is methyl, R² isbromine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 133 covers compounds of formula (AH), wherein R¹ is ethyl, R² ischlorine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 134 covers compounds of formula (AH), wherein R¹ is ethyl, R² isbromine, R³ is hydrogen, R⁴ is methoxy, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 135 covers compounds of formula (AH), wherein R¹ and R⁴ aremethyl, R² is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 136 covers compounds of formula (AH), wherein R¹ is methyl, R² ismethoxy, R³ is hydrogen, R⁴ is ethyl, R⁵ and R¹² are hydrogen and R⁶,R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 137 covers compounds of formula (AH), wherein R¹ and R⁴ are ethyl,R² is methoxy, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ areas defined in Table 74.

Table 138 covers compounds of formula (AH) wherein R¹, R², R³ and R⁴ aremethyl, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹ are as definedin Table 74.

Table 139 covers compounds of formula (A), wherein R¹ isdifluoromethoxy, R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen andR⁶, R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 140 covers compounds of formula (A), wherein R¹ isdifluoromethoxy, R² is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogenand R⁶, R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 141 covers compounds of formula (A), wherein R¹ istrifluoromethoxy, R² and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen andR⁶, R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 142 covers compounds of formula (A), wherein R¹ istrifluoromethoxy, R² is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogenand R⁶, R⁸, R⁹, and R¹¹ are as defined in Table 74.

Table 143 covers compounds of formula (A), wherein R¹ is cyclopropyl, R²and R⁴ are methyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Table 144 covers compounds of formula (A), wherein R¹ is cyclopropyl, R²is methyl, R⁴ is ethyl, R³, R⁵ and R¹² are hydrogen and R⁶, R⁸, R⁹, andR¹¹ are as defined in Table 74.

Table 145 covers compounds of formula (A), wherein R¹ and R² are methyl,R³, R⁵ and R¹² are hydrogen, R⁴ is cyclopropyl and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Table 146 covers compounds of formula (A), wherein R¹ and R² are ethyl,R³, R⁵ and R¹² are hydrogen, R⁴ is cyclopropyl and R⁶, R⁸, R⁹, and R¹¹are as defined in Table 74.

Example 25 Preparation of(1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-3-en-3-yl2,2-dimethylpropionate

A solution of pivaloyl chloride (0.055 g, 0.57 mmol) in dichloromethane(2 ml) is added dropwise to a solution of(1RS,2SR,6RS,7SR)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione(0.12 g, 0.42 mmol) in dichloromethane (2 ml) at room temperature andthe reaction mixture is stirred for 2 minutes. A solution oftriethylamine (0.08 ml) in dichloromethane (1 ml) is added and thereaction mixture is stirred at room temperature for 3 hours. Thereaction mixture is diluted with dichloromethane (20 ml) and washed withsaturated aqueous sodium bicarbonate solution. The organic phase isdried over anhydrous magnesium sulfate, filtered and the filtrateevaporated under reduced pressure to give(1RS,2SR,6RS,7SR)-5-oxo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]dec-3-en-3-yl2,2-dimethylpropionate as a colourless oil.

¹H NMR (400 MHz, CDCl₃) δ_(H) 6.84 (1H, s), 6.82 (1H, s), 4.75 (1H, d),4.55 (1H, d), 3.45 (1H, d), 2.78 (1H, d), 2.24 (3H, s), 2.09 (3H, s),2.02 (3H, s), 1.89-1.83 (2H, m), 1.63-1.59 (2H, m), 1.11 (9H, s).

Example 26 Preparation of carbonic acid(1RS,2SR,6RS,7SR)-5-oxo-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]-dec-3-en-3-ylester ethyl ester

A solution of ethyl chloroformate (0.071 g, 0.65 mmol) indichloromethane (0.5 ml) is added dropwise to a solution of(1RS,2SR,6RS,7SR)-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo[5.2.1.0^(2,6)]decane-3,5-dione(0.172 g, 0.55 mmol) in dichloromethane (2 ml) at 0° C. and the reactionmixture is stirred. A solution of triethylamine (0.066 g, 0.65 mmol) indichloromethane (1 ml) is added and the reaction mixture is stirred atroom temperature for 17 hours, warming slowly to room temperature. Thereaction mixture is diluted with dichloromethane (3 ml) and washed withsaturated aqueous sodium bicarbonate solution. The organic phase isseparated, dried over anhydrous magnesium sulfate, filtered and thefiltrate evaporated under reduced pressure. The residue is purified bycolumn chromatography on silica gel to give carbonic acid (1RS,2SR,6RS,7SR)-5-oxo-4-(2,6-diethyl-4-methylphenyl)-10-oxatricyclo-[5.2.1.0^(2,6)]-dec-3-en-3-ylester ethyl ester as a colourless solid.

¹H NMR (400 MHz, CDCl₃) δ_(H) 1.06 (6H, m), 1.28 (3H, t), 1.63 (2H, m),1.87 (2H, m), 2.3 (3H, s), 2.35 (4H, m), 2.8 (1H, d), 3.63 (1H, d), 4.22(2H, q), 4.64 (1H, d), 4.77 (1H, d), 6.91 (2H, d).

Additional compounds in Table P1 below were prepared by similar methodsusing appropriate starting materials.

TABLE P1 Compound ¹H nmr (CDCl₃ unless stated) or other physical NumberStructure data P1

δ_(H) 6.90 (2H, s), 6.45 (1H, dd), 6.35 (1H, dd), 5.30 (1H, d), 5.25(1H, d), 3.65 (3H, s), 3.65 (1H, dd), 3.45 (1H, dd), 2.35 (4H, m), 2.30(3H, s), 1.10 (6H, m). P2

δ_(H) 6.90 (2H, m), 4.85 (2H, m), 3.70 (3H, s), 3.60 (1H, m), 3.35 (1H,dd), 2.50 (2H, m), 2.35 (2H, m), 2.30 (3H, s), 1.90-1.75 (4H, m), 1.20(3H, t), 1.10 (3H, t) P3

δ_(H) 6.87 (1H, s), 6.85 (1H, s), 4.74 (1H, d), 4.68 (2H, t), 4.65 (1H,d), 3.53 (1H, d), 2.79 (1H, d), 2.56 (1H, t), 2.26 (3H, s), 2.09 (3H,s), 2.05 (3H, s), 1.94-1.80 (2H, m), 1.67-1.56 (2H, m). P4

δ_(H) 6.87 (1H, s), 6.85 (1H. s), 4.85-4.78 (1H, m), 4.74 (1H, d), 4.64(1H, d), 3.51 (1H, d), 2.77 (1H, d), 2.25 (3H, s), 2.09 (3H, s), 2.06(3H, s), 1.93- 1.79 (2H, m), 1.67-1.54 (2H, m), 1.25 (3H, d), 1.20 (3H,d). P5

δ_(H) 6.88 (1H, s), 6.86 (1H, s), 4.73 (1H, d), 4.59 (1H, d), 3.56 (1H,d), 2.76 (1H, d), 2.27 (3H, s), 2.10 (3H, s), 2.04 (3H, s), 1.89-1.80(2H, m), 1.69-1.56 (3H, m), 1.01-0.92 (4H, m). P6

δ_(H) 6.86 (1H, s), 6.84 (1H, s), 4.74 (1H, d), 4.58 (1H, d), 3.48 (1H,d), 2.77 (1H, d), 2.40-2.35 (2H, m), 2.26 (3H, s), 2.09 (3H, s), 2.04(3H, s), 1.93- 1.82 (2H, m), 1.65-1.48 (4H, m), 1.31-1.17 (6H, m), 0.86(3H, t). P7

δ_(H) 7.38-7.37 (3H, m), 7.19-7.18 (2H, m), 6.97 (2H, s), 6.68 (1H, dd),6.55 (1H, d), 5.08 (1H, s with fine splitting), 4.82-4.81 (2H, m),4.13-4.10 (1H, m), 4.03-4.00 (1H, m), 3.13 (1H, dd), 2.89 (1H, dd),2.54-2.45 (4H, m), 2.37 (3H, s), 1.20- 1.16 (6H, m). P8

δ_(H) 7.35-7.32 (3H, m), 7.15-7.13 (2H, m), 6.93 (1H, s), 6.92 (1H, s),6.54-6.49 (2H, m), 5.14 (1H, d), 4.71-4.64 (2H, m), 4.15-4.08 (2H, m),2.99 (1H, d), 2.84 (1H, d), 2.59-2.39 (4H, m), 2.32 (3H, s), 1.17-1.13(6H, m). P9

δ_(H) 6.84 (1H, s), 6.82 (1H, s), 4.73 (1H, d), 4.57- 4.55 (1H, m),3.46-3.44 (1H, m), 2.77 (1H, d), 2.46-2.35 (1H, m), 2.23 (3H, s), 2.08(3H, s), 2.02 (3H, s), 1.92-1.80 (2H, m), 1.04 (3H, d), 0.93 (3H, t).P10

δ_(H) 6.86 (1H, s), 6.84 (1H, s), 4.74 (1H, d), 4.56 (1H, d), 3.49 (1H,d), 2.78 (1H, d), 2.65-2.58 (1H, m), 2.25 (3H, s), 2.09 (3H, s), 2.03(3H, s), 1.93- 1.79 (2H, m), 1.66-1.56 (2H, m), 1.13 (3H, d), 1.06 (3H,d). P11

δ_(H) 7.34-7.31 (3H, m), 7.15-7.12 (2H, m), 6.90 (2H, s), 6.50 (2H, s),5.05 (1H, s), 4.79-4.72 (4H, m), 4.23 (1H, d), 3.97 (1H, d), 3.65-3.58(2H, m), 3.06 (1H, d), 2.66 (1H, d), 2.54-2.34 (4H, m), 2.31 (3H, s),1.20 (3H, t), 1.15-1.10 (6H, m). P12

δ_(H) 7.33-7.30 (3H, m), 7.14-7.12 (2H, m), 6.90 (2H, s), 6.51 (1H, dd),6.45 (1H, d), 5.11 (1H, d), 5.05 (1H, d), 4.81-4.76 (1H, m), 4.73-4.72(2H, m), 4.30 (1H, d), 3.17-3.12 (2H, m), 3.06 (1H, d), 2.69 (1H, d),2.52-2.35 (4H, m), 2.31 (3H, s), 1.53-1.47 (2H, m), 1.15-1.11 (6H, m),0.90 (3H, t). P13

δ_(H) 7.33-7.30 (3H, m), 7.15-7.11 (2H, m), 6.86 (2H, s), 6.50-6.49 (2H,m), 5.11 (0.5H, s), 5.04 (0.5H, s), 4.76-4.66 (2H, m), 4.16-4.11 (1H,m), 3.77-3.74 (1H, m), 3.43 (1.5H, s), 3.34 (1.5H, s), 3.03 (0.5H, s),2.94 (0.5H, s), 2.77 (0.5H, d), 2.62 (0.5H, d), 2.27 (1.5H, s), 2.19(1.5H, s), 2.12 (1.5H, s), 2.08 (1.5H, s), 2.07 (3H, s). P14

δ_(H) 1.04 (6H, m), 1.08 (9H, s), 1.6 (2H, m), 1.85 (2H, m), 2.3 (3H,s), 2.33 (4H, m), 2.79 (1H, d), 3.58 (1H, d), 4.54 (1H, d), 4.74 (1H,d), 6.85 (1H, s) 6.88 (1H, s). P15

δ_(H) 1.04 (6H, m), 1.6 (2H, m), 1.85 (2H, m), 2.3 (3H, s), 2.35 (4H,m), 2.8 (1H, d), 3.63 (1H, d), 4.66 (1H, d), 4.7 (1H, s), 4.75 (1H, d),6.9 (2H, s). P16

δ_(H) 1.04 (6H, m), 1.2 (3H, m), 1.35 (1H, m), 1.6 (8H, m), 1.85 (2H,m), 2.32 (9H, m), 2.8 (1H, d), 3.58 (1H, d), 3.67 (3H, s), 4.58 (1H, d),4.75 (1H, d), 6.9 (2H, s). P17

δ_(H) 1.04 (6H, m), 1.3-1.8 (14H, m), 2.3 (3H, s), 2.34 (5H, m), 2.79(1H, d), 3.6 (1H, d), 4.54 (1H, d), 4.75 (1H, d), 6.89 (2H, d). P18

δ_(H) 1.06 (6H, m), 1.28 (3H, t), 1.63 (2H, m), 1.87 (2H, m), 2.3 (3H,s), 2.35 (4H, m), 2.8 (1H, d), 3.63 (1H, d), 4.22 (2H, q), 4.64 (1H, d),4.77 (1H, d), 6.91 (2H, d). P19

δ_(H) 0.85 (6H, d), 1.05 (6H, m), 1.61 (2H, m), 1.85 (2H, m), 1.98 (1H,m), 2.28 (2H, d), 2.3 (3H, s), 2.35 (4H, m), 2.8 (1H, d), 3.58 (1H, d),4.58 (1H, d), 4.75 (1H, d), 6.89 (2H, d). P20

δ_(H) 0.84 (3H, t), 1.05 (6H, m), 1.23 (8H, m), 1.62 (2H, m), 1.86 (2H,m), 2.3 (3H, s), 2.37 (6H, m), 2.8 (1H, d), 3.59 (1H, d), 4.58 (1H, d),4.75 (1H, d), 6.9 (2H, d). P21

δ_(H) 0.95 (4H, m), 1.05 (6H, m), 1.63 (3H, m), 1.85 (2H, m), 2.3 (3H,s), 2.35 (4H, m), 2.77 (1H, d), 3.65 (1H, d), 4.59 (1H, d), 4.74 (1H,d), 6.9 (2H, d) P22

δ_(H) 1.07 (9H, m), 1.6 (2H, m), 1.85 (2H, m), 2.31 (3H, s), 2.39 (6H,m), 2.79 (1H, d), 3.62 (1H, d), 4.58 (1H, d), 4.74 (1H, d), 6.9 (2H, d).P23

δ_(H) 1.06 (6H, m), 1.62 (2H, m), 1.87 (2H, m), 2.3 (3H, s), 2.35 (4H,m), 2.8 (1H, d), 3.52 (1H, d), 4.62 (3H, m), 4.75 (1H, d), 5.31 (2H, m),5.85 (1H, m), 6.91 (2H, d). P24

δ_(H) 0.9 (6H, d), 1.07 (6H, m), 1.61 (2H, m), 1.86 (2H, m), 1.92 (1H,m), 2.31 (3H, s), 2.32 (4H, m), 2.8 (1H, d), 3.52 (1H, d), 3.94 (2H, m),4.64 (1H, d), 4.76 (1H, d), 6.91 (2H, d). P25

δ_(H) 1.07 (6H, m), 1.62 (2H, m), 1.87 (2H, m), 2.31 (3H, s), 2.36 (4H,m), 2.56 (1H, m), 2.81 (1H, d), 3.63 (1H, d), 4.67 (1H, d), 4.75 (2H,m), 6.9 (2H, d). P26

δ_(H) 1.05 (9H, m), 1.13 (3H, d), 1.61 (2H, m), 1.87 (2H, m), 2.31 (3H,s), 2.36 (4H, m), 2.6 (1H, m), 2.79 (1H, d) 3.61 (1H, d), 4.57 (1H, d),4.76 (1H, d), 6.89 (2H, d). P27

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.87-6.86 (2H, m),4.84-4.77 (1H, m), 4.60 (1H, d), 3.89 (1H, d), 3.70 (1H, d), 3.60 (1H,d), 3.41 (3H, s), 2.80 (1H, d), 2.25 (3H, s), 2.10 (3H, s), 2.05 (3H,s), 2.03-1.96 (2H, m), 1.72-1.65 (2H, m), 1.25 (3H, d), 1.19 (3H, d).

P28

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.88-6.86 (2H, m),4.74-4.60 (3H, m), 3.89- 6.63 (3H, m), 3.41 (3H, s), 2.92 (0.5H, d),2.83- 2.81 (0.5H, m), 2.56-2.55 (1H, m), 2.26 (3H, s), 2.10 (1.5H, 5),2.09 (1.5H, s), 2.04 (1.5H, s), 2.03 (1.5H, s), 2.00-1.65 (4H, m).

P29

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.86-6.84 (2H, m),4.55 (1H, d), 3.89 (1H, d), 3.70 (1H, d), 3.59 (1H, d), 3.41 (3H, s),2.81 (1H, d), 2.39-2.33 (2H, m), 2.25 (3H, s), 2.09 (3H, s), 2.03 (3H,s), 2.00-1.95 (1H, m), 1.66-1.49 (3H, m), 1.38-1.13 (8H, m), 0.90-0.84(3H, m).

P30

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.88-6.86 (2H, m),4.55 (1H, d), 3.89 (1H, d), 3.71-3.65 (2H, m), 3.41 (3H, s), 2.79 (1H,d), 2.27 (3H, s), 2.11 (3H, s), 2.03 (3H, s), 1.78-1.50 (4H, m),1.07-1.04 (1H, m), 0.99-0.91 (4H, m).

P31

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.84-6.82 (2H, m),4.54-4.52 (1H, m), 3.89 (1H, d), 3.70 (1H, d), 3.56 (1H, t), 3.40 (3H,s), 2.80 (1H, d), 2.44-2.37 (1H, m), 2.24 (3H, s), 2.09 (3H, s), 2.02(3H, s), 1.71-1.35 (6H, m), 1.17-1.02 (3H, m), 0.95-0.67 (3H, m).

P32

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.85-6.83 (2H, m),4.52 (1H, d), 3.89 (1H, d), 3.70 (1H, d), 3.58 (1H, d), 3.40 (3H, s),2.80 (1H, d), 2.62-2.57 (1H, m), 2.24 (3H, s), 2.09 (3H, s), 2.02 (3H,s), 1.71-1.52 (4H, m), 1.11 (3H, t), 1.04 (3H, d).

P33

δ_(H) 6.84 (1H, s), 6.82 (1H, s), 4.75 (1H, d), 4.55 (1H, d), 3.45 (1H,d), 2.78 (1H, d), 2.24 (3H, s), 2.09 (3H, s), 2.02 (3H, s), 1.89-1.83(2H, m), 1.63- 1.59 (2H, m), 1.11 (9H, s). P34

δ_(H) 6.90 (1H, s), 6.89 (1H, s), 4.73 (1H, d), 4.66 (1H, d), 3.58 (3H,s), 2.91 (1H, d), 2.66 (1H, d), 2.49-2.39 (4H, m), 2.30 (3H, s),1.88-1.81 (2H, m), 1.62-1.56 (2H, m), 1.12-1.08 (3H, m). P35

δ_(H) 6.93 (2H, br. s), 3.71-3.69 (1H, m), 2.81-2.80 (1H, m), 2.33 (3H,s), 2.20 (3H, s), 2.08 (3H, s), 1.87-1.72 (5H, m), 1.64-1.60 (6H, m),1.05- 0.99 (4H, m). P36

δ_(H) 6.88 (1H, s), 6.86 (1H, s), 4.71 (1H, dd), 4.61 (1h, dd), 3.65(1H, d), 2.77 (1H, d), 2.55 (1H, t), 2.26 (3H, s), 2.12 (3H, s), 2.04(3H, s), 1.82-1.71 (4H, m), 1.56 (3H, s), 1.53 (3H, s). P37

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.87 (1H, s), 6.85(1H, s), 4.70 (0.5H, d), 4.55 (0.5H, d), 4.43 (1H, s), 4.26 (1H, s),3.53 (1H, app t), 2.74 (1H, app t), 2.26 (3H, s), 2.09 (3H, s), 2.04(3H, s), 1.82-1.63 (3H, m), 1.49-1.41 (2H, m), 1.30-1.26 (1H, m),0.98-0.90 (7H, m).

P38

Approximately 1:1 ratio of Isomer A:Isomer B δ_(H) 6.87 (1H, s), 6.86(1H, s), 4.72-4.60 (3H, m), 4.45 (0.5H, s), 4.33 (0.5H, d), 3.77 (1H,s), 3.50 (1H, d), 2.79-2.76 (0.5H, m), 2.56-2.54 (0.5H, m), 2.26 (3H,s), 2.08 (3H, s), 2.05 (3H, s), 1.84- 1.75 (2H, m), 1.52-1.42 (2H, m),1.30-1.24 (1H, m), 0.96-0.83 (3H, m).

P39

δ_(H) 7.01 (1H, br. s), 6.76 (1H, d), 6.72 (1H, dd), 4.72 (1H, d), 4.65(1H, d), 3.78 (3H, s), 3.65 (3H, s), 2.88 (1H, d), 2.64 (1H, d), 2.15(3H, s), 1.80- 1.89 (2H, m), 1.56-1.62 (2H, m). P40

δ_(H) 6.91 (1H, br. s), 6.76 (1H, s), 6.70 (1H, d), 4.73 (1H, d), 4.53(1H, d), 3.78 (3H, s), 3.43 (1H, s), 2.75 (1H, d), 2.15 (3H, s),1.93-1.79 (2H, m), 1.65-1.58 (2H, m), 1.16 (9H, s). P41

δ_(H) 7.11-7.05 (1H, m), 7.03-6.99 (1H, m), 6.89 (1H, br. s), 4.73 (1H,d), 4.65 (1H, d), 3.64 (1H, s), 2.89 (1H, d), 2.64 (1H, d), 2.28 (3H,s), 2.13 (3H, s), 1.92-1.78 (2H, m), 1.63-1.57 (2H, m). P42

δ_(H) 7.19 (1H, dd), 6.96 (1H, td), 6.91-6.86 (1H, m), 4.77 (1H, d),4.70 (1H, d), 3.72 (3H, s), 2.96 (1H, d), 2.70 (1H, d), 2.18 (3H, s),1.97-1.82 (2H, m), 1.68-1.62 (2H, m). P43

δ_(H) 7.16-7.10 (1H, m), 7.08-7.03 (1H, m), 6.94 (1H, br. s), 4.77 (1H,d), 4.70 (11-1, d), 3.68 (3H, s), 2.93 (1H, d), 2.72-2.66 (1H, m), 2.17(3H, s), 1.97-1.80 (2H, m), 1.62-1.58 (2H, m). P44

δ_(H) 7.09 (1H, d), 7.04-6.99 (1H, m), 6.76 (1H, br. s), 4.75 (1H, d),4.54 (1H, d), 3.49-3.41 (1H, m), 2.76 (1H, d), 2.26 (3H, s), 2.17 (3H,s), 1.94-1.79 (2H, m), 1.67-1.59 (2H, m), 1.15 (9H, s). P45

δ_(H) 7.16 (1H, dd), 6.92 (1H, td), 6.74 (1H, br. s), 4.75 (1H, d), 4.54(1H, d), 3.46 (1H, d), 2.77 (1H, d), 2.17 (3H, s), 1.93-1.82 (2H, m),1.67-1.57 (2H, m), 1.17 (9H, s). P46

δ_(H) 7.21-7.17 (1H, m), 7.16-7.12 (1H, m), 6.96 (1H, br. s), 4.74 (1H,d), 4.54 (1H, s), 3.45 (1H, d), 2.77 (1H, d), 2.17 (3H, s), 1.94-1.80(2H, m), 1.67-1.58 (2H, m), 1.17 (9H, s). P47

δ_(H) 6.58 (2H, d), 4.74 (1H, d), 4.55 (1H, d), 3.76 (3H, s), 3.43 (1H,d), 2.82-2.73 (1H, m), 2.11 (3H, s), 2.04 (3H, s), 1.93-1.78 (2H, m),1.66-1.57 (2H, m), 1.11 (9H, s). P48

δ_(H) 7.33 (1H, d), 7.29 (1H, br. s), 7.23 (1H, dd), 4.75 (1H, d), 4.67(1H, d), 3.76 (3H, s), 2.94 (1H, s), 2.69 (1H, s), 1.93-1.79 (2H, m),1.65-1.54 (2H, m). P49

δH 6.60 (2H, d), 4.72 (1H, d), 4.65 (1H, d), 3.76 (3H, s), 3.58 (3H, s),2.88 (1H, d), 2.64 (1H, d), 2.13 (3H, s), 2.10 (3H, s), 1.90-1.77 (2H,m), 1.64- 1.54 (2H, m). P50

δ_(H) 7.14 (2H, d), 5.34 (1H, s), 5.04 (1H, s), 4.73 (1H, d), 4.66 (1H,d), 3.58 (3H, s), 2.90 (1H, d), 2.66 (1H, d), 2.17 (3H, s), 2.14 (3H,s), 2.11 (3H, s), 1.92-1.75 (2H, m), 1.66-1.54 (2H, m). P51

Approximately 1:1 mixture of Isomer A:Isomer B Isomer A: δ_(H) 7.81 (2H,s), 6.87 (1H, s), 6.83 (1H, s), 4.83 (1H, d), 4.69 (1H, s), 3.64 (1H,d), 3.22 (1H, dd), 2.99 (1H, d), 2.38 (1H, dd), 2.25 (3H, s), 2.11 (3H,s), 2.04 (3H, s), 1.99-1.96 (1H, m), 1.23 (3H, s), 1.13 (6H, s). IsomerB: δ_(H) 7.84 (2H, s), 6.87 (1H, s), 6.84 (1H, s), 4.99 (1H, d), 4.50(1H, s), 3.64 (1H, d), 3.24 (1H, dd), 2.94 (1H, d), 2.35 (1H, dd), 2.25(3H, s), 2.10 (3H, s), 2.04 (3H, s), 1.91-1.89 (1H, m), 1.07 (9H s).

P52

Approximately 1:1:1:1 mixture of Isomer A:Isomer B:Isomer C:Isomer Dδ_(H) 6.84 (1H, s), 6.82 (1H, s), 4.71 (0.25H, d), 4.68 (0.25H, d), 4.60(0.25H, d), 4.52 (0.25H, d), 4.48 (0.25H, d), 4.45 (0.25H, s), 4.41(0.25H, d), 4.23 (0.25H, s), 3.79 (0.25H, d), 3.43 (0.514, t), 3.04(0.25H, d), 2.77-2.73 (0.75H, m), 2.24 (3H, s), 2.19-2.11 (1H, m), 2.09(3H, s), 2.03 (3H, s), 1.84-1.73 (1H, m), 1.52-1.39 (2H, m), 1.28- 1.26(1H, m), 1.12-1.10 (9H, m), 1.00-0.90 (3H, m).

Biological Examples Test Example 1

Monocotyledonous and dicotyledonous test plants were sown in standardsoil in pots. After cultivation for one day (pre-emergence) or after 10days cultivation (post-emergence) under controlled conditions in aglasshouse, the plants were sprayed with an aqueous spray solutionderived from the formulation of the technical active ingredient in 0.6ml acetone and 45 ml formulation solution containing 10.6% Emulsogen EL(Registry number 61791-12-6), 42.2% N-methylpyrrolidone, 42.2%dipropylene glycol monomethyl ether (Registry number 34590-94-8) and0.2% X-77 (Registry number 11097-66-8). The test plants were then grownin a greenhouse under optimum conditions until, 15 days later forpost-emergence and 20 days for pre-emergence, the test was evaluated(100=total damage to plant; 0=no damage to plant).

Test Plants:

Alopecurus myosuroides (ALOMY), Avena fatua (AVEFA), Lolium perenne(LOLPE), Setaria faberi (SETFA), Digitaria sanguinalis (DIGSA),Echinochloa crus-galli (ECHCG)

Pre-Emergence Activity

Compound Rate Number g/ha ALOMY AVEFA LOLPE SETFA DIGSA ECHCG T1 250 100100 100 100 100 100 T2 250 100 100 100 90 100 100 T3 250 90 80 100 70 80100 T4 250 90 90 100 90 100 100 T5 250 100 80 100 80 100 100 T6 250 8030 100 80 90 90 T7 250 100 80 100 90 80 90 T8 250 100 90 100 100 100 100T9 250 70 40 100 100 100 100 T10 250 80 70 100 80 80 90 T11 250 30 40 6020 0 30 T12 250 10 10 40 40 40 0 T13 250 80 80 90 100 100 100 T14 250 9090 100 100 70 90 T15 250 40 20 40 60 30 80 T16 250 0 10 0 10 0 0 T17 250100 90 100 100 100 100 T18 250 100 100 100 100 100 100 T19 250 100 90100 100 90 100 T21 250 90 30 80 70 10 80 T27 250 70 70 70 100 90 100 T34250 70 30 60 80 60 40 T37 250 60 30 30 0 20 30 T39 250 10 20 30 40 30 30T40 250 50 60 60 40 60 40 T41 250 50 30 20 60 30 70 T42 250 0 10 0 0 030 T43 250 10 20 0 50 20 0 T44 250 80 40 70 80 80 70 T46 250 10 0 30 3020 70 T47 250 100 80 100 80 70 100 T48 250 100 80 100 100 100 100 T49250 80 70 100 20 10 80 T52 250 40 30 100 90 90 100 T53 250 10 20 10 1010 0 T56 250 100 60 100 70 70 100 T57 250 50 30 100 80 60 70 T58 250 010 0 0 0 60 T59 250 10 20 30 40 50 30 T60 250 0 40 10 10 30 30 T62 25070 70 60 80 80 80 T64 250 0 0 10 20 10 50 T65 250 100 90 100 90 100 100T66 250 30 60 40 100 90 70 T70 250 80 50 100 90 90 100 T71 250 30 0 0 2050 50 T85 250 40 60 70 70 60 70 T89 250 20 60 40 30 30 20 T90 250 10 6020 40 60 70 T91 250 20 50 20 50 70 50 T92 250 20 60 30 70 70 90 T93 25040 30 20 30 30 0 T97 250 100 90 100 90 100 100 T98 250 30 20 20 70 0 30T99 250 80 60 100 80 80 100 T106 250 90 90 100 100 100 100 T107 250 9090 100 100 100 100 T125 250 70 70 100 100 100 100 T128 250 70 70 90 100100 100 T129 250 100 90 90 100 90 100 T134 250 60 20 70 0 50 20 T143 25050 20 70 70 80 10 T146 250 70 60 90 80 80 80 T147 250 40 0 40 60 40 90T148 250 60 50 70 60 70 80 T149 250 90 60 80 80 70 90 T150 250 0 0 30 00 40 T151 250 50 20 60 20 80 40 T153 250 70 70 80 70 60 70 T154 250 7050 80 70 70 100 T155 250 60 50 80 60 70 60 T156 250 70 60 70 70 70 70T157 250 30 — 70 0 0 50 T158 250 60 50 70 70 70 50 T159 250 50 60 40 7070 70 T160 250 30 50 40 70 40 40 T162 250 70 70 90 10 40 80 T163 250 7060 90 90 90 80 T165 250 70 20 80 70 50 80 T167 250 30 40 40 0 30 50 T169250 20 30 40 0 0 0 T170 250 80 40 90 70 70 80 T171 250 30 0 10 70 40 70T173 250 90 70 100 60 70 70 T174 250 30 30 30 0 40 0 T177 250 60 50 7050 10 70 T178 250 70 40 80 100 80 100 T179 250 70 60 80 10 60 70 T180250 30 20 70 40 80 60 T181 250 40 40 80 70 90 100 T182 250 30 50 40 5080 90 T184 250 30 60 70 90 70 60 T185 250 80 80 100 80 80 80 T187 250 1020 60 40 20 10 T188 250 40 0 50 70 100 60 T193 250 20 30 60 40 20 20T194 250 0 20 20 50 70 50 T199 250 0 50 60 60 100 80 T200 250 0 0 70 7070 90 T203 250 20 20 60 70 70 90 T208 250 50 70 80 80 70 80 P3 250 100100 100 90 90 100 P4 250 100 100 100 70 90 90 P5 250 100 100 100 90 10090 P6 250 100 100 100 80 100 90 P9 250 100 100 100 80 90 80 P10 250 100100 100 80 100 100 P14 250 100 100 100 100 100 100 P15 250 80 90 90 100100 100 P16 250 100 90 90 100 100 100 P17 250 90 90 100 100 100 100 P18250 100 100 100 100 100 100 P19 250 100 100 100 100 100 100 P20 250 10080 100 100 100 100 P21 250 100 100 100 100 100 100 P22 250 100 100 100100 100 100 P23 250 80 90 100 100 100 100 P24 250 90 90 100 100 100 100P25 250 100 100 100 100 100 100 P26 250 100 90 100 100 100 100 P27 25090 80 90 80 90 100 P28 250 90 80 100 80 90 80 P30 250 80 80 90 80 80 90P33 250 90 70 100 80 80 — P36 250 70 80 100 80 80 100 P37 250 90 90 100100 100 100Post-Emergence Activity

Compound Rate Number g/ha ALOMY AVEFA LOLPE SETFA DIGSA ECHCG T1 125 9090 80 100 100 100 T2 125 100 90 100 80 100 100 T3 125 60 30 60 90 100100 T4 125 80 90 90 80 80 100 T5 125 70 70 80 90 100 100 T6 125 80 80 8080 90 90 T7 125 100 90 90 90 70 90 T8 125 100 100 100 100 100 100 T9 12580 60 70 80 100 100 T10 125 70 70 80 80 50 80 T11 125 40 20 30 70 80 70T12 125 70 50 10 70 70 70 T13 125 80 90 90 100 50 100 T14 125 80 80 80100 90 100 T15 125 50 40 40 50 80 80 T16 125 40 20 50 0 0 30 T17 125 100100 90 100 100 100 T18 125 100 100 80 100 100 100 T19 125 100 100 90 10090 100 T21 125 90 70 70 60 30 100 T27 125 100 90 80 100 100 100 T34 12540 30 30 80 80 80 T37 125 50 20 20 70 50 80 T39 125 10 20 0 60 70 70 T40125 40 30 30 70 70 70 T41 125 40 0 0 80 80 80 T42 125 0 0 10 0 20 60 T43125 10 0 0 40 20 60 T44 125 80 50 20 80 80 90 T46 125 0 0 0 60 0 80 T47125 100 90 90 70 60 100 T48 125 80 70 70 90 100 100 T49 125 80 80 70 5070 80 T52 125 60 70 70 80 80 100 T56 125 100 50 80 60 70 100 T57 125 7070 40 70 70 80 T58 125 0 10 0 30 40 30 T59 125 50 40 0 70 80 80 T60 12510 0 0 40 50 0 T62 125 60 0 20 70 70 80 T64 125 10 0 0 30 60 50 T65 12590 90 80 100 100 100 T66 125 80 80 50 80 90 80 T70 125 90 70 70 70 70 80T71 125 50 10 20 50 70 60 T85 125 90 20 70 70 20 100 T89 125 80 80 80 9090 100 T90 125 90 80 60 60 80 80 T91 125 90 90 50 100 100 100 T92 125100 100 50 100 100 100 T93 125 60 80 60 100 100 100 T97 125 90 90 80 100100 100 T98 125 70 20 40 70 60 80 T99 125 80 30 10 70 60 100 T106 125 9080 80 90 80 100 T107 125 100 90 90 100 100 100 T125 125 80 70 70 80 8090 T128 125 80 90 80 100 100 100 T129 125 80 80 70 100 80 100 T134 12520 20 20 50 20 70 T143 125 40 60 30 40 60 70 T146 125 80 80 90 70 70 100T147 125 90 90 40 70 100 90 T149 125 80 90 70 70 80 100 T150 125 60 6040 90 30 100 T151 125 80 80 30 10 70 80 T153 125 50 80 50 20 30 70 T154125 90 60 60 70 70 100 T155 125 90 70 60 100 100 100 T156 125 90 80 70100 70 100 T157 125 60 60 40 60 60 100 T158 125 90 90 80 100 100 100T159 125 90 70 40 100 100 100 T160 125 90 90 70 100 100 100 T162 125 9090 70 100 100 100 T163 125 80 80 80 90 70 100 T165 125 80 30 80 90 70100 T167 125 80 50 50 70 70 100 T169 125 90 10 30 60 40 80 T170 125 8070 80 40 40 100 T171 125 70 60 20 90 80 100 T173 125 100 90 90 90 70 100T174 125 70 70 40 50 70 80 T177 125 80 70 30 20 30 80 T178 125 100 90 90100 100 100 T179 125 80 80 80 10 50 70 T180 125 90 70 70 100 90 100 T181125 90 90 80 100 80 100 T182 125 100 90 80 100 100 100 T184 125 10 0 1050 20 100 T185 125 90 80 80 100 100 100 T187 125 70 10 40 60 60 70 T188125 80 70 30 70 100 100 T193 125 60 40 30 30 60 60 T194 125 30 0 20 0 7080 T199 125 100 100 60 80 100 100 T200 125 70 80 80 100 100 100 T203 12520 10 10 0 50 50 T208 125 70 70 80 70 50 80 P3 125 100 90 100 80 70 100P4 125 100 90 100 90 80 100 P5 125 100 90 100 80 60 100 P6 125 100 90100 80 80 100 P9 125 100 90 100 80 80 90 P10 125 100 90 100 80 80 100P14 125 90 90 90 100 100 100 P15 125 100 90 90 80 80 100 P16 125 100 90100 100 100 100 P17 125 100 90 100 100 100 100 P18 125 90 50 80 70 70100 P19 125 100 100 100 100 100 100 P20 125 100 100 100 90 80 100 P21125 90 100 100 100 80 100 P22 125 100 100 100 100 100 100 P23 125 100 9090 80 70 100 P24 125 100 100 100 100 70 100 P25 125 100 90 100 80 80 100P26 125 100 100 90 100 100 100 P24 125 80 60 70 90 100 90 P28 125 80 8070 80 80 100 P30 125 80 NC 70 80 90 100 P33 125 80 70 80 70 70 90 P36125 60 70 60 80 80 90 P37 125 90 80 90 100 90 100

Test Example 2

Test compounds were applied post-emergence at 60 g ai/ha, alone and incombination with cloquintocet-mexyl at 60 g ai/ha; the adjuvant Adigor(0.5%) was included for every treatment. The application volume was2001/ha. Target plants were 2-3 leaf seedlings of winter wheat‘Hereward’ and winter barley ‘Antoniya’ grown in a greenhouse underambient conditions. Assessments were made at 14-21 days afterapplication.

Cloquintocet- Rate mexyl Crop Injury (%) Compound (g/ha) (g/ha) WheatBarley T1 60 0 85 99 60 60 18 73 T3 60 0 28 5 60 60 0 5 1:1 mixture of60 0 63 85 T106:T107 60 60 23 45

Test Example 3

The test compound T1 was applied at 100 and 200 g ai/ha, alone and incombination with a range of safeners as 1:1 mixtures (for example at 100g+100 g; 200 g+200 g) to the test plants—wheat and maize—at the 2-3 leafstage. A 4-way safener mixture (cloquintocet-mexyl, benoxacor,fluxofenim and compound A*) was also applied with the test compound sothat each safener was used a 1:1 ratio (for example at100+100+100+100+100 g ai/ha). Assessments were made at 14-21 days afterapplication.

Wheat Injury (%) Maize Injury (%) Test Sample 100 g/ha 200 g/ha 100 g/ha200 g/ha T1 alone 83 92 90 100 T1 + benoxacor at 1:1 80 85 90 75 ratioT1 + cloquintocet-mexyl 5 10 93 95 at 1:1 ratio T1 + isoxadifen at 1:165 73 65 75 ratio T1 + cyprosulfamide 68 85 23 28 at 1:1 ratio T1 +compound A* at 73 88 30 35 1:1 ratio T1 + fluxofenim at 1:1 75 90 85 88ratio T1 + mefenpyr-diethyl 23 45 100 100 at 1:1 ratio T1 + dichlormidat 1:1 73 73 80 100 ratio T1 + 4-way mix at 0 20 30 50 1:1:1:1 ratio*Compound A isN-(2-methoxybenzoyl)-4-[(methylaminocarbonyl)amino]benzenesulfonamide.

What is claimed is:
 1. A compound of formula I

wherein G is hydrogen or an alkali metal, alkaline earth metal, sulfonium, ammonium or a latentiating group, R¹ is methyl, ethyl, n-propyl, isopropyl, cyclopropyl, halomethyl, haloethyl, vinyl, ethynyl, halogen, C₁-C₂alkoxy or C₁-C₂haloalkoxy, R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl, n-propyl, isopropyl, cyclopropyl, halomethyl, haloethyl, vinyl, ethynyl, halogen, C₁-C₂alkoxy or C₁-C₂ haloalkoxy, R⁵ and R¹² are independently of each other hydrogen, C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkyoxy, C₁-C₃alkylthio, halogen or C₁-C₆alkoxycarbonyl, or R⁵ and R¹² join together to form a 3-7 membered carbocyclic ring, optionally containing an oxygen or sulfur atom, and wherein R⁶ and R¹¹ are independently of each other hydrogen, halogen, formyl, cyano or nitro or R⁶ and R¹¹ are independently of each other C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₃-C₇ cycloalkyl, C₃-C₇ cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, or R⁶ and R¹¹ are independently of each other a group COR¹³, CO₂R¹⁴ or CONR¹⁵R¹⁶, CR¹⁷═NOR¹⁸, CR¹⁹═NNR²⁰R²¹, NHR²², NR²²R²³ or OR²⁴, wherein R¹³ is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, R¹⁴ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or is 3-7 membered heterocyclyl, where all these substituents are optionally substituted, R¹⁵ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, and R¹⁶ is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, C₁-C₆alkylsulfonyl, phenylsulfonyl, heteroarylsulfonyl, C₁-C₆alkylamino, diC₁-C₆alkylamino, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, or amino, or R¹⁵ and R¹⁶ are joined to form an optionally substituted 3-7 membered ring, optionally containing an oxygen, sulfur or nitrogen atom, and R¹⁷ and R¹⁹ are independently of each other hydrogen, C₁-C₃alkyl or C₃-C₆cycloalkyl, R¹⁸, R²⁰ and R²¹ are independently of each other hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, phenyl or heteroaryl, where all these substituents are optionally substituted, or aminocarbonyl, and R²² is C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl, phenylcarbonyl, phenoxycarbonyl, phenylaminocarbonyl, phenylthiocarbonyl, phenylsulfonyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylaminocarbonyl, heteroarylthiocarbonyl or heteroarylsulfonyl, where all these substituents are optionally substituted, and R²³ is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl, phenyl or heteroaryl, where all these substituents are optionally substituted, or R²² and R²³ are joined to form an optionally substituted 3-7 membered ring, optionally containing an oxygen, sulfur or nitrogen atom, where all these substituents are optionally substituted, and R²⁴ is C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, tri(C₁-C₆alkyl)silyl, phenyl or heteroaryl, where all these substituents are optionally substituted, or aminocarbonyl; and wherein R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen, halogen, hydroxyl, formyl, amino, cyano or nitro, or R⁷, R⁸, R⁹ and R¹⁰ are independently of each other C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl, C₁-C₆alkylthio, C₁-C₆alkylsulfinyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylthioC₁-C₆alkyl, C₁-C₆alkylsulfinylC₁-C₆alkyl, C₁-C₆alkylsulfonylC₁-C₆alkyl, C₃-C₇ cycloalkyl, C₄-C₇cycloalkenyl, tri(C₁-C₆alkyl)silyl, aryl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, or R⁷, R⁸, R⁹ and R¹⁰ are independently of each other a group COR^(13A), CO₂R^(14A) or CONR^(15A)R^(16A), CR^(17A)═NOR^(18A), CR^(19A)═NNR^(20A)R^(21A), NR^(22A)R^(23A) or OR^(24A), or R⁷ and R⁸, or R⁹ and R¹⁰, together form a unit ═O, or form a unit ═CR²⁵R²⁶, or form a unit ═NR²⁷, or any two of R⁷, R⁸, R⁹ and R¹⁰ form a 3-8 membered ring, optionally containing a heteroatom selected from O, S and N and optionally substituted by: C₁-C₃alkyl, C₁-C₃alkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, C₁-C₃haloalkyl, halogen, phenyl; phenyl substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, aminocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, halogen, cyano or by nitro; or heteroaryl or heteroaryl substituted by C₁-C₄alkyl, C₁-C₄haloalkyl, C₁-C₄alkoxy, C₁-C₄haloalkoxy, C₁-C₄alkylthio, C₁-C₄alkylsulfinyl, C₁-C₄alkylsulfonyl, C₁-C₄alkylcarbonyl, halogen, cyano or by nitro, or R⁷ and R¹⁰ together form a bond; and wherein R^(13A) is C₁-C₆alkyl, C₂-C₆alkenyl, C₂-C₆alkynyl, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, R^(14A) is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or is 3-7 membered heterocyclyl, where all these substituents are optionally substituted, R^(15A) is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, and R^(16A) is hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₁-C₆alkoxy, C₁-C₆haloalkoxy, C₃-C₇ cycloalkyl, C₅-C₇cycloalkenyl, C₁-C₆alkylsulfonyl, C₁-C₆alkylamino, diC₁-C₆alkylamino, phenyl, heteroaryl or a 3-7 membered heterocyclyl, where all these substituents are optionally substituted, or amino, or R^(15A) and R^(16A) are joined to form an optionally substituted 3-7 membered ring, optionally containing an oxygen, sulfur or nitrogen atom, and R^(17A) and R^(19A) are independently of each other hydrogen, C₁-C₃alkyl or C₃-C₆cycloalkyl, R^(18A), R^(20A) and R^(21A) are independently of each other hydrogen, C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, phenyl or heteroaryl, where all these substituents are optionally substituted, and R^(22A) and R^(23A) are independently of each other C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl, phenyl or heteroaryl, or R^(22A) and R^(23A) are joined to form an optionally substituted 3-7 membered ring, optionally containing an oxygen, sulfur or nitrogen atom, where all these substituents are optionally substituted, and R^(24A) is C₁-C₆alkyl, C₃-C₆alkenyl, C₃-C₆alkynyl, C₃-C₇ cycloalkyl, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylthiocarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, C₁-C₆alkylsulfonyl, tri(C₁-C₆alkyl)silyl, phenyl or heteroaryl, where all these substituents are optionally substituted; and wherein R²⁵ and R²⁶ are independently of each other hydrogen, halogen, cyano or nitro, or R²⁵ and R²⁶ are independently of each other C₁-C₆alkyl, C₁-C₆alkoxy, C₁-C₆alkylamino, diC₁-C₆alkylamino, C₁-C₆alkylcarbonyl, C₁-C₆alkoxycarbonyl, C₁-C₆alkylaminocarbonyl, diC₁-C₆alkylaminocarbonyl, N-phenyl-N—C₁-C₆alkylaminocarbonyl, N-phenylC₁-C₆alkyl-N—C₁-C₆alkylaminocarbonyl, N-heteroaryl-N—C₁-C₆alkylaminocarbonyl, N-heteroarylC₁-C₆alkyl-N—C₁-C₆alkylaminocarbonyl, phenyl, heteroaryl, C₃-C₈cycloalkyl or 3-7 membered heterocyclyl, where all these substituents are optionally substituted, or R²⁵ and R²⁶ are joined together to form a 5-8 membered ring optionally containing a heteroatom selected from O, S and N and optionally substituted by C₁-C₂alkyl or C₁-C₂alkoxy, and R²⁷ is nitro or cyano, or R²⁷ is C₁-C₆alkylamino, diC₁-C₆alkylamino, C₁-C₆alkoxy, C₃-C₆alkenyloxy, C₃-C₆alkynyloxy, phenoxy, phenylamino, N-phenyl-N—C₁-C₆alkylamino, N-phenylC₁-C₆alkyl-N—C₁-C₆alkylamino, heteroaryloxy, heteroarylamino, N-heteroaryl-N—C₁-C₆alkylamino or N-heteroarylC₁-C₆alkyl-N—C₁-C₆alkylamino, where all these substituents are optionally substituted; and wherein, when G is a latentiating group then G is selected from the groups phenylC₁alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; heteroarylC₁alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; C₃ alkenyl, C₃ haloalkenyl, C₃ alkynyl, C(X^(a)_—R^(a), C(X^(b))—X^(c)—R^(b), C(X^(d))—N(R^(c))—R^(d), —SO₂—R^(e), —P(X^(e))(R^(f))—R^(g) and CH₂—X^(f)—R^(h); wherein X^(a), X^(b), X^(c), X^(d), X^(e) and X^(f) are independently of each other oxygen or sulfur; and wherein R^(a) is H, C₁-C₁₈alkyl, C₂-C₁₈alkenyl, C₂-C₁₈alkynyl, C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynylC₁-C₅oxyalkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; C₂-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; R^(b) is C₁-C₁₈alkyl, C₃-C₁₈alkenyl, C₃-C₁₈alkynyl, C₂-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; C₃-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; and R^(c) and R^(d) are each independently of each other hydrogen, C₁-C₁₀alkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₂-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; C₂-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; diheteroarylamino or diheteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; diphenylamino or diphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; or C₃-C₇cycloalkylamino, di-C₃-C₇cycloalkylamino or C₃-C₇cycloalkoxy; or R^(c) and R^(d) may join together to form a 3-7 membered ring, optionally containing one heteroatom selected from O and S; and R^(e) is C₁-C₁₀alkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; C₂-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; diheteroarylamino or diheteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino, C₃-C₇cycloalkoxy, C₁-C₁₀alkoxy, C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₈dialkylamino; R^(f) and R^(g) are are each independently of each other C₁-C₁₀alkyl, C₂-C₁₀alkenyl, C₂-C₁₀alkynyl, C₁-C₁₀alkoxy, C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₁-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₂-C₅alkylaminoalkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃alkylsulfonyl, halogen, cyano, or by nitro; C₂-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; heteroaryl or heteroaryl substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; heteroarylamino or heteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; diheteroarylamino or diheteroarylamino substituted by C₁-C₃ alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; phenylamino or phenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; diphenylamino or diphenylamino substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; or C₃-C₇cycloalkylamino, diC₃-C₇cycloalkylamino, C₃-C₇cycloalkoxy, C₁-C₁₀haloalkoxy, C₁-C₅alkylamino or C₂-C₈dialkylamino; or benzyloxy or phenoxy, wherein the benzyl and phenyl groups may in turn be substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or nitro; and R^(h) is C₁-C₁₀alkyl, C₃-C₁₀alkenyl, C₃-C₁₀alkynyl, C₁-C₁₀haloalkyl, C₁-C₁₀cyanoalkyl, C₁-C₁₀nitroalkyl, C₂-C₁₀aminoalkyl, C₁-C₅alkylaminoC₁-C₅alkyl, C₂-C₈dialkylaminoC₁-C₅alkyl, C₃-C₇cycloalkylC₁-C₅alkyl, C₁-C₅alkoxyC₁-C₅alkyl, C₃-C₅alkenyloxyC₁-C₅alkyl, C₃-C₅alkynyloxyC₁-C₅alkyl, C₁-C₅alkylthioC₁-C₅alkyl, C₁-C₅alkylsulfinylC₁-C₅alkyl, C₁-C₅alkylsulfonylC₁-C₅alkyl, C₂-C₈alkylideneaminoxyC₁-C₅alkyl, C₁-C₅alkylcarbonylC₁-C₅alkyl, C₁-C₅alkoxycarbonylC₁-C₅alkyl, aminocarbonylC₁-C₅alkyl, C₁-C₅alkylaminocarbonylC₁-C₅alkyl, C₂-C₈dialkylaminocarbonylC₁-C₅alkyl, C₁-C₅alkylcarbonylaminoC₁-C₅alkyl, N—C₁-C₅alkylcarbonyl-N—C₁-C₅alkylaminoC₁-C₅alkyl, C₃-C₆trialkylsilylC₁-C₅alkyl; phenylC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; heteroarylC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; phenoxyC₁-C₅alkyl wherein the phenyl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; heteroaryloxyC₁-C₅alkyl wherein the heteroaryl is optionally substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, C₁-C₃alkylthio, C₁-C₃alkylsulfinyl, C₁-C₃ alkylsulfonyl, halogen, cyano or by nitro; C₃-C₅haloalkenyl, C₃-C₈cycloalkyl; phenyl or phenyl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen or by nitro; or heteroaryl or heteroaryl substituted by C₁-C₃alkyl, C₁-C₃haloalkyl, C₁-C₃alkoxy, C₁-C₃haloalkoxy, halogen, cyano or by nitro; and wherein, when present, optional substituents on an alkyl moiety, either alone or as part of a larger group, are selected from one or more of halogen, nitro, cyano, C₃₋₇ cycloalkyl optionally substituted with C₁₋₆ alkyl or halogen, C₅₋₇ cycloalkenyl optionally substituted with C₁₋₆ alkyl or halogen, hydroxy, C₁₋₁₀ alkoxy, C₁₋₁₀ alkoxy(C₁₋₁₀)alkoxy, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkoxy, C₁₋₆ alkoxycarbonyl(C₁₋₁₀)alkoxy, C₁₋₁₀ haloalkoxy, aryl(C₁₋₄)-alkoxy where the aryl group is optionally substituted, C₃₋₇ cycloalkyloxy where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen, C₃₋₁₀ alkenyloxy, C₃₋₁₀ alkynyloxy, mercapto, C₁₋₁₀ alkylthio, C₁₋₁₀ haloalkylthio, aryl(C₁₋₄)alkylthio where the aryl group is optionally substituted, C₃₋₇ cycloalkylthio where the cycloalkyl group is optionally substituted with C₁₋₆ alkyl or halogen, tri(C₁₋₄)alkylsilyl(C₁₋₆)alkylthio, arylthio where the aryl group is optionally substituted, C₁₋₆ alkylsulfonyl, C₁₋₆ haloalkylsulfonyl, C₁₋₆ alkylsulfinyl, C₁₋₆ haloalkylsulfinyl, arylsulfonyl where the aryl group is optionally substituted, tri(C₁₋₄)alkylsilyl, aryldi(C₁₋₄)alkylsilyl, (C₁₋₄)alkyldiarylsilyl, triarylsilyl, aryl(C₁₋₄)alkylthio(C₁₋₄)alkyl, aryloxy(C₁₋₄)alkyl, formyl, C₁₋₁₀ alkylcarbonyl, HO₂C, C₁₋₁₀ alkoxycarbonyl, aminocarbonyl, C₁₋₆ alkylaminocarbonyl, di(C₁₋₆ alkyl)aminocarbonyl, N—(C₁₋₃ alkyl)-N—(C₁₋₃ alkoxy)aminocarbonyl, C₁₋₆ alkylcarbonyloxy, arylcarbonyloxy where the aryl group is optionally substituted, di(C₁₋₆)alkylaminocarbonyloxy, C₁₋₆alkyliminooxy, C₃₋₆alkenyloxyimino, aryloxyimino, optionally substituted aryl, optionally substituted heteroaryl heterocyclyl optionally substituted with C₁₋₆ alkyl or halogen, aryloxy where the aryl group is optionally substituted, heteroaryloxy where the heteroaryl group is optionally substituted, heterocyclyloxy where the heterocyclyl group is optionally substituted with C₁₋₆ alkyl or halogen, amino, C₁₋₆ alkylamino, di(C₁₋₆)alkylamino, C₁₋₆ alkylcarbonylamino, N—(C₁₋₆)alkylcarbonyl-N—(C₁₋₆)alkylamino, C₂₋₆ alkenylcarbonyl, C₂₋₆ alkynylcarbonyl, C₃₋₆ alkenyloxycarbonyl, C₃₋₆ alkynyloxycarbonyl, aryloxycarbonyl where the aryl group is optionally substituted, and arylcarbonyl where the aryl group is optionally substituted; wherein, when present, optional substituents on alkenyl or alkynyl are selected from those optional substituents defined above for an alkyl moiety; wherein, when present, optional substituents on cycloalkyl or cycloalkenyl are selected from C₁₋₃ alkyl and those optional substituents defined above for an alkyl moiety; wherein, when present, the optional substituents on aryl, heteroaryl and carbocycles, unless otherwise indicated, are selected, independently, from: halogen, nitro, cyano, isothiocyanato, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁alkoxy(C₁₋₆)alkyl, C₂₋₆ alkenyl, C₂₋₆ haloalkenyl, C₂₋₆ alkynyl, C₃ cycloalkyl optionally substituted with C₁ alkyl or halogen, C₅₋₇ cycloalkenyl optionally substituted with C₁ alkyl or halogen, hydroxy, alkoxy within which the alkyl moiety is C₁-C₃ alkyl, C₁alkoxy(C₁)alkoxy, C₁alkoxycarbonyl(C₁)alkoxy, C₁ haloalkoxy, C₃ alkenyloxy, C₃ alkynyloxy, mercapto, C₁ alkylthio, C₁ haloalkylthio, C₁ alkylsulfonyl, C₁ haloalkylsulfonyl, C₁ alkylsulfinyl, C₁ haloalkylsulfinyl, C₁ alkylcarbonyl, HO₂C, C₁ alkoxycarbonyl, aminocarbonyl, C₁ alkylaminocarbonyl, di(C₁alkyl)aminocarbonyl, N—(C₁alkyl)-N—(C₁alkoxy)aminocarbonyl, C₁ alkylcarbonyloxy, di(C₁)alkylamino-carbonyloxy, amino, C₁ alkylamino, di(C₁)alkylamino, C₁ alkylcarbonylamino, and N—C₁alkylcarbonyl)—N—(C₁alkyl)amino; wherein, for substituted heterocyclyl groups then the one or more substituents are independently selected from halogen, C₁₋₆ alkyl, C₁₋₆ haloalkyl, C₁₋₆ alkoxy, C₁₋₆ haloalkoxy, C₁₋₆ alkylthio, C₁₋₆ alkylsulfinyl, C₁₋₆ alkylsulfonyl, nitro and cyano; and wherein “heterocyclyl” means a non-aromatic monocyclic or bicyclic ring system containing up to 7 atoms including one or two heteroatoms selected from O, S and N; wherein “aryl” means phenyl; and wherein “heteroaryl” means an aromatic ring system containing at least one heteroatom and consisting either of a single ring or of two fused rings.
 2. A compound according to claim 1, wherein R¹, R² and R⁴ are methyl and R³ is hydrogen.
 3. A compound according to claim 1, wherein R¹, R² and R⁴ are methyl and R³ is hydrogen, and R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl, 3-7 membered heterocyclyl, optionally substituted aryl or optionally substituted heteroaryl.
 4. A compound according to claim 1, wherein R⁵ and R¹² are independently of each other hydrogen or C₁-C₃alkyl.
 5. A compound according to claim 1, wherein R¹ is methyl, ethyl, vinyl, ethynyl, cyclopropyl, difluoromethoxy, trifluoromethoxy or C₁-C₂ alkoxy and R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl, vinyl or ethynyl.
 6. A process for the preparation of a compound of formula (AH)

wherein R¹, R², R³, R⁴, R⁵, R⁶, R⁸, R⁹, R¹¹ and R¹² are as defined in claim 1, which comprises reacting a compound of formula (H)

with a compound of formula (AI)

in the presence or absence of a catalyst and in the presence or absence of a solvent.
 7. A herbicidal composition, which, in addition to comprising at least one formulation adjuvant, comprises a herbicidally effective amount of a compound of formula I as defined in claim
 1. 8. A herbicidal composition according to claim 7, which, in addition to comprising at least one formulation adjuvant, comprises a herbicidally effective amount of a compound of formula I and a further herbicide.
 9. A herbicidal composition according to claim 7, which, in addition to comprising at least one formulation adjuvant, comprises a herbicidally effective amount of a compound of formula I, a further herbicide and a safener.
 10. A method of controlling grasses and weeds in crops of useful plants, which comprises applying a herbicidally effective amount of a compound of formula I as defined in claim 1, or of a composition comprising such a compound, to the plants or to the locus thereof.
 11. A compound according to claim 1, wherein R⁶ and R¹¹ are independently of each other hydrogen, methyl or methyl substituted by C₁-C₃alkoxy.
 12. A compound according to claim 1, wherein R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen, cyano, C₁-C₆alkyl, C₂-C₆alkenyl, C₁-C₆alkoxy, C₁-C₆alkoxyC₁-C₆alkyl, 3-7 membered heterocyclyl, optionally substituted phenyl or optionally substituted heteroaryl.
 13. A compound according to claim 12, wherein R⁷, R⁸, R⁹ and R¹⁰ are independently of each other hydrogen, methyl, ethyl or optionally substituted phenyl.
 14. A compound according to claim 12, wherein one of R⁷, R⁸, R⁹ and R¹⁰ is furyl, thienyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl or quinoxalinyl, wherein each of these heteroaryls is optionally substituted.
 15. A compound according to claim 14, wherein one of R⁷, R⁸, R⁹ and R¹⁰ is pyridyl substituted once or twice by trifluoromethyl or halogen.
 16. A compound according to claim 1, wherein: R⁵ and R¹² are independently of each other hydrogen or C₁-C₃alkyl; and R⁶ and R¹¹ are independently of each other hydrogen, methyl or methyl substituted by C₁-C₃alkoxy; and wherein R⁷, R⁸, R⁹ and R¹³ are independently of each other hydrogen, cyano, C₁-C₆alkyl, C₂alkenyl, C₁alkoxy, C₁alkoxyC₁alkyl, optionally substituted phenyl or optionally substituted heteroaryl; provided that: either (a) R⁷, R⁸, R⁹ and R¹³ are independently of each other hydrogen, methyl, ethyl or optionally substituted phenyl; or (b) one of R⁷, R⁸, R⁹ and R¹³ is furyl, thienyl, pyrazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, cinnolinyl, quinazolinyl or quinoxalinyl, wherein each of these heteroaryls is optionally substituted.
 17. A compound according to claim 16, wherein R⁵ and R¹² are hydrogen.
 18. A compound according to claim 17, wherein R⁷, R⁸, R⁹ and R¹⁰ are hydrogen.
 19. A compound according to claim 17, wherein R¹ is methyl, ethyl, vinyl, ethynyl, cyclopropyl, difluoromethoxy, trifluoromethoxy or C₁-C₂ alkoxy, and R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl, vinyl or ethynyl.
 20. A compound according to claim 18, wherein R¹ is methyl, ethyl, vinyl, ethynyl, cyclopropyl, difluoromethoxy, trifluoromethoxy or C₁-C₂ alkoxy, and R², R³ and R⁴ are independently of each other hydrogen, methyl, ethyl, vinyl or ethynyl. 